Oxo-substituted compound

ABSTRACT

Provided is a novel compound that has an excellent β-lactamase inhibitory effect. More specifically, provided is a compound represented by formula (1a), (1b) or (11) having an excellent β-lactamase inhibitory effect or a pharmaceutically acceptable salt thereof. By using this compound either in combination with a β-lactam drug or alone, a useful preventive or therapeutic agent for bacterial infections is provided. Also provided are useful preventive or therapeutic agents for treating various diseases with the combined use of the aforesaid compound and β-lactam drugs.

This application is a continuation of application Ser. No. 17/050,747, filed Oct. 26, 2020, which is a national stage application of PCT/JP2019/018011, filed Apr. 26, 2019, which claims priority to JP 2018-087761, filed Apr. 27, 2018, the contents of each application are incorporated herein by reference in their entirety.

TECHNICAL FIELD

The present invention relates to an oxo-substituted compound that is useful as a medicament or a pharmaceutically acceptable salt thereof. More specifically, the present invention relates to a pharmaceutical composition comprising a novel oxo-substituted compound or a pharmaceutically acceptable salt thereof. The present invention relates to a therapeutic agent comprising the oxo-substituted compound or a pharmaceutically acceptable salt thereof.

BACKGROUND ART

Since the discovery of penicillin, antimicrobial agents have taken an important role in the treatment of infections.

In particular, β-lactam agents (e.g., penicillin antimicrobial agents, cephalosporin antimicrobial agents, and carbapenem antimicrobial agents) are agents that are most commonly used in the treatment of bacterial infections in view of their potent sterilizing capacity and high degree of safety. However, with increased use of β-lactam agents, emergence and prevalence of pathogenic bacteria that have acquired resistance to β-lactam agents have become a global problem. Examples of the mechanism of acquiring resistance of such pathogens include production of β-lactamase, structural change in the target molecule of a β-lactam agent, reduced drug permeation into microbial cell, elevated drug discharge, and the like. In particular, production of β-lactamase, which degrades and inactivates β-lactam agents, is one of the most influential in the maintenance of efficacy of β-lactam agents. Various bacteria are involved in the evolution of β-lactamase that antagonizes the efficacy of various β-lactam agents. β-lactamases can be classified into 4 classes based on their amino acid sequences, i.e., Ambler classes A, B, C, and D. Since class A, C, and D enzymes have a serine residue at the center of enzymatic activity, they are known as serine-β-lactamases. Since class B enzymes do not have a serine residue at the center of enzymatic activity but have metal ion zinc (Zn²⁺), they are known as metallo-β-lactamases (zinc-β-lactamases).

It has been already confirmed that concomitant use of a β-lactamase inhibiting agent and a β-lactam agent is effective for solving the problem of resistance acquisition due to production of β-lactamase. It is known that commercially available β-lactamase inhibiting agents clavulanic acid, sulbactam, and tazobactam primarily inhibit class A β-lactamases excluding KPC (Klebsiella pneumoniae Carbapenemase), and avibactam inhibits class A β-lactamases (including KPC), class C β-lactamases, and some class D β-lactamases including OXA-48 (Non Patent Literature 1). However, these existing β-lactamase inhibiting agents cannot effectively and broadly inhibit all β-lactamases produced by various bacteria. For example, such inhibiting agents do not exert an effect on class B metallo-β lactamases. Recently, β-lactamases called ESBLs (Extended Spectrum β-Lactamases) that can degrade more substrates (β-lactam agent) compared to conventional β-lactamases were isolated, which have led to a problem as a new resistant bacteria, especially as a causative bacteria for hospital-acquired infections in the US and Europe. In addition, emergence and prevalence of metallo-β-lactamase producing bacteria is becoming a problem in Japan. In view of such a circumstance, it is very important to address β-lactamase producing bacteria including ESBLs and metallo-β-lactamase for the prophylaxis of hospital-acquired infections. Furthermore, pathogenic bacteria evolve quickly, such that emergence of new β-lactamase resistant bacteria is very likely. Accordingly, as a solution to such problems or as a safeguard against such issues to be addressed, there is a demand for the development of a novel BS-lactamase inhibiting agent that has a different structure from existing β-lactamase inhibiting agents, whereby a broader β-lactamase inhibitory action or metallo-β-lactamase inhibitory action is expected.

Recently, boronic acid derivatives with β-lactamase inhibitory action have been reported in Patent Literatures 1 to 9 and the like. These Patent Literatures do not disclose a structure related to the oxo-substituted compounds encompassed by the present invention, i.e., a boronic acid compound group having a non-aryl heterocycle (preferably a nitrogen-containing non-aryl heterocycle) on a side chain at a specific position and an oxo substituent (—C(═O)—, —S(═O)—, —S(═O)₂—, or the like) that attaches to the ring.

CITATION LIST Patent Literature

-   [PTL 1] WO 2014/107535 -   [PTL 2] WO 2014/107536 -   [PTL 3] WO 2015/179308 -   [PTL 4] WO 2016/003929 -   [PTL 5] WO 2016/149393 -   [PTL 6] WO 2014/089365 -   [PTL 7] WO 2014/110442 -   [PTL 8] WO 2014/151958 -   [PTL 9] WO 2015/191907

Non Patent Literature

-   [NPL 1] Buynak. J D. Expert Opinion on Therapeutic Patents, 2013,     23(11), 1469-1481.

SUMMARY OF INVENTION Solution to Problem

The present invention provides a novel compound having excellent β-lactamase inhibitory action and provides a prophylactic or therapeutic agent that is useful for a bacteria infection, alone or in concomitant use with a β-lactam agent. Specifically, the present invention provides a prophylactic or therapeutic agent that is useful for therapy, by concomitant use with a β-lactam agent, of a disease such as sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, urinary tract infection, genital infection, eye infection, or odontogenic infection.

More specifically, the inventors completed the present invention by finding that a compound represented by formula (1a), (1b), or (11) described below or a pharmaceutically acceptable salt thereof (also referred to as the “compound of the invention” hereinafter) has excellent β-lactamase inhibitory action. Specifically, the present invention is the following.

[Item A1]

A compound represented by formula (1a) or (1b):

or a pharmaceutically acceptable salt thereof wherein

G is an oxygen atom, a sulfur atom, or —NR^(a1)—,

X is a hydroxyl group, an optionally substituted C₁₋₆ alkoxy group, or —NR^(a2)R^(b1),

R^(a1), R^(a2), and R^(b1) are the same or different, each independently

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl,

6) a 4- to 10-membered non-aryl heterocycle,

7) a C₁₋₆ alkylcarbonyl group,

8) a C₃₋₁₀ alicyclic carbonyl group,

9) a C₆₋₁₀ arylcarbonyl group,

10) a 5- or 6-membered heteroarylcarbonyl group,

11) a C₁₋₆ alkylsulfonyl group,

12) a C₃₋₁₀ alicyclic sulfonyl group,

13) a C₆₋₁₀ arylsulfonyl group,

14) a 5- or 6-membered heteroarylsulfonyl group, or

15) —OR^(c1),

(wherein each substituent from 2) to 14) is optionally substituted),

wherein R^(a2) and R^(b1) together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(c1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle, (wherein each substituent from 2) to 6) is optionally substituted),

L¹ is a single bond, an oxygen atom, a sulfur atom, —SO—, —SO₂—, —NR^(d)—, —NR^(d)C(═O)—, or —NR^(d)SO₂—,

L² is a single bond or an optionally substituted C₁₋₆ alkylene group,

Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a carboxyl group,

5) a C₃₋₁₀ alicyclic group,

6) C₆₋₁₀ aryl,

7) 5- or 6-membered heteroaryl,

8) a 4- to 10-membered non-aryl heterocycle,

9) a C₁₋₆ alkoxy group,

10) a C₃₋₁₀ alicyclic oxy group,

11) a C₆₋₁₀ aryloxy group,

12) a 5- or 6-membered heteroaryloxy group,

13) a 4- to 10-membered non-aryl heterocyclyl oxy group,

14) a C₁₋₆ alkylthio group,

15) a C₃₋₁₀ alicyclic thio group,

16) a C₆₋₁₀ arylthio group,

17) a 5- or 6-membered heteroarylthio group,

18) a 4- to 10-membered non-aryl heterocyclyl thio group,

(wherein each substituent from 5) to 18) is optionally substituted),

19) —SO₂—NR^(e1)R^(f1),

20) —NR^(e1)—C(═O)OR^(f1),

21) —NR^(g1)—C(═O)NR^(e1)R^(f1),

22) —NR^(e1)—C(═S)OR^(f1),

23) —NR^(e1)—C(═S)OR^(f1),

24) —NR^(g1)—C(═S)NR^(e1)R^(f1),

25) —NR^(g1)—CR^(e1)(═NR^(f1)),

26) —NR^(g1)—CR^(e1)(═N—OR^(f1)),

27) —NR^(h1)—C(═NR^(g1))NR^(e1)R^(f1),

28) —NR^(h1)—C(═N—OR^(g1))NR^(e1)R^(f1),

29) —NR^(i1)—C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

30) —NR^(i1)—C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

31) —NR^(e1)—SO₂—R^(f1),

32) —NR^(g1)—SO₂—NR^(e1)R^(f1),

33) —C(═O)OR^(e1),

34) —C(═S)OR^(e1),

35) —C(═S)NR^(e1)R^(f1),

36) —C(═S)NR^(e1)OR^(f1),

37) —C(═S)NR^(g1)—NR^(e1)R^(f1),

38) —C(═NR^(e1))R^(f1),

39) —C(═N—OR^(e1))R^(f1),

40) —C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

41) —C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

42) —NR^(e1)R^(f1)

43) —NR^(g1)—NR^(e1)R^(f1),

44) —NR^(e1)OR^(f1),

45) —NR^(e1)—C(═O)R^(f1),

46) —C(═O)NR^(e1)R^(f1),

47) —C(═O)NR^(e1)OR^(f1),

48) —C(═O)NR^(g1)—NR^(e1)R^(f1),

49) —C(═O)PR^(e1),

50) —C(═NR^(g1))NR^(e1)R^(f1), or

51) —C(═N—OR^(h1))NR^(e1)R^(f1),

one of R¹, R², and R³ is a group represented by formula (2):

wherein

Y is an oxygen atom, a sulfur atom, or —NR^(j)—,

ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle,

L³ is —C(═O)—, —S(═O)—, or —S(═O)₂—,

L⁴ is

1) a single bond,

2) a C₁₋₆ alkylene group,

3) a C₃₋₁₀ cycloalkylene group,

4) a C₆₋₁₀ arylene group

5) a 5- or 6-membered heteroarylene group,

6) a 4- to 10-membered non-aryl heterocyclylene group, or

7) —C(═N—OR^(h1))—

(wherein each substituent from 2) to 6) is optionally substituted), and

R⁵ is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) a 4- to 10-membered non-aryl heterocycle,

5) C₆₋₁₀ aryl,

6) 5- or 6-membered heteroaryl,

7) a C₁₋₆ alkylthio group,

(wherein each substituent from 2) to 7) is optionally substituted), or

8) —NR^(e1)OH,

the remaining two (without the structure of formula (2) among R¹, R², and R³) are the same or different, each independently a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted C₁₋₆ alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR^(a3)R^(b2),

R^(d), R^(e1), R^(e2), R^(f1), R^(f2), R^(g1), R^(g2), R^(h1), R^(h2), R^(i1), R^(i2), and R^(j) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₃₋₁₀ alicyclic group, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle,

a combination of R^(e1) and R^(f1) or R^(e2) and R^(f2), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R⁴ is

1) —C(═O)R⁸,

2) —SO₂-L⁶-R⁸,

(wherein R⁸ in 1) and 2) is —NR^(a5)R^(b4), —NR^(a5)-L⁷-B(OR^(m1))₂, —OR^(m1), or an optionally substituted C₁₋₆ alkyl group, and L⁶ is a single bond or —NR^(a6)—),

3) —NR^(a4)R^(b3),

4) —B(OR^(m1))₂,

5) —PO(OR^(m1)) (OR^(m2))

6) optionally substituted 5-membered heteroaryl,

7) an optionally substituted 5-membered non-aryl heterocycle, or

8) a bioisostere of one of 1) to 7),

(wherein the formulas of 2), 4), 5), and 6) include a carboxylic acid isostere, and 8) may include them in duplicates),

R^(a3), R^(a4), R^(a5), R^(a6), R^(b2), R^(b3), and R^(b4) are the same or different, each independently having the same definition as R^(a1), R^(a2), and RUT, wherein a combination of R^(a1) and R^(b2), R^(a4) and R^(b3), or R^(a5) and R^(b4), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(m1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle

(wherein each substituent from 2) to 6) is optionally substituted),

wherein if R^(m1) is attached to a boron atom via an oxygen atom, two R^(m1), as C₂₋₄ alkylene, together with the boron atom and two oxygen atoms, may form a 5- to 7-membered non-aryl heterocycle (wherein an alkylene moiety is optionally substituted in the non-aryl heterocycle),

R^(m2) is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group, and

L⁷ is an optionally substituted C₁₋₃ alkylene group.

[Item A2]

The compound or the pharmaceutically acceptable salt thereof according to item A1, wherein

L¹ is a single bond, a sulfur atom, —NR^(d)C(═O)—, or —NR^(d)SO₂—,

L² is a single bond or an optionally substituted C₁₋₆ alkylene group, and

Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl,

6) a 4- to 10-membered non-aryl heterocycle,

7) —C(═N—OR^(e1))R^(f1), or

8) —NR^(e1)R^(f1).

[Item A3]

The compound or the pharmaceutically acceptable salt thereof according to item A1 or A2, wherein

Z-L²-L¹ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₁₋₆ alkylthio group.

[Item A4]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A3, wherein Z-L²-L¹ is a hydrogen atom.

[Item A5]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A4, wherein G is an oxygen atom.

[Item A6]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A5, wherein X is a hydroxyl group or an optionally substituted C₁₋₆ alkoxy group.

[Item A7]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A6, wherein X is a hydroxyl group.

[Item A8]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A7, wherein the compounds of formulas (1a) and (1b) are represented by formulas (3a) and (3b), respectively:

wherein X, R¹, R², and R³ are defined the same as any one of items A1 to A7, and

R⁴ is selected from the group consisting of

1) —COOR^(m1) (wherein R^(m1) is a hydrogen atom, a C_(1_6) alkyl group, a C₃₋₁₀ alicyclic group, C₆₋₁₀ aryl, 5- or 6-membered heteroaryl, or a 4- to 10-membered non-aryl heterocycle, and wherein the C₁₋₆ alkyl group, the C₃₋₁₀ alicyclic group, the C₆₋₁₀ aryl, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle are each optionally substituted), and 2) a bioisostere of 1). [Item A9]

The compound or the pharmaceutically acceptable salt thereof according to item A8, wherein R⁴ is

1) —COOH (i.e., a carboxyl group), or

2) a carboxylic acid isostere.

[Item A10]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A9, wherein the compounds of formulas (1a) and (1b) or the compounds of formulas (3a) and (3b) are represented by formulas (4a) and (4b), respectively:

wherein X, R⁴, Y, ring A, L³, L⁴, and R⁵ are defined the same as any one of items A1 to A9, and

R¹ and R² are the same or different, each independently a hydrogen atom, a halogen atom, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group (wherein the C₁₋₆ alkyl group and C₁₋₆ alkoxy group are optionally substituted with 1 to 5 halogen atoms).

[Item A11]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A10, wherein ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle.

[Item A12]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A11, wherein ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle.

[Item A13]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A12, wherein Y is an oxygen atom or a sulfur atom.

[Item A14]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A13, wherein Y is an oxygen atom.

[Item A15]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A14, wherein the compounds of formulas (1a) and (1b), the compounds of formulas (3a) and (3b), or the compounds of formulas (4a) and (4b) are represented by formulas (5a) and (5b), respectively:

wherein ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle. [Item A16]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A15, wherein L³ is —C(═O)— or —S(═O)₂—.

[Item A17]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A16, wherein L³ is —C(═O)—.

[Item A18]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A17, wherein L⁴ is a single bond, —C(═N—OR^(h1))—, or an optionally substituted C₁₋₆ alkylene group, wherein R^(h1) is an optionally substituted C₁₋₆ alkyl group.

[Item A19]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A18, wherein L⁴ is a single bond, or a C₁₋₆ alkylene group optionally substituted with —NR²¹R²² or ═NOR²³, wherein R²¹, R²², and R²³ are each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted 4- to 10-membered non-aryl heterocyclyl carbonyl group.

[Item A20]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A19, wherein L⁴ is a single bond, —CH₂—, —CH(NH₂)—, or —CH(NH₂)—CH₂—, wherein if an amino group is present in L⁴, carbon that attaches to the amino group attaches to L³.

[Item A21]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A20, wherein R⁵ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, an optionally substituted C₁₋₆ alkylthio group, or —NR^(e1)OH, wherein R^(e1) is a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item A22]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A21, wherein R⁵ is optionally substituted 5- or 6-membered heteroaryl or optionally substituted C₆₋₁₀ aryl.

[Item A23]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A21, wherein L⁴ is a single bond, and R⁵ is —NR^(e1)OH, wherein R^(e1) is a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item A24]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A22, wherein

R⁵ is selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) halogen,

5) a C₁₋₄ alkyl group,

6) a C₃₋₁₀ alicyclic group,

7) a C₁₋₄ alkoxy group,

8) a C₃₋₁₀ alicyclic oxy group,

9) a C₆₋₁₀ aryloxy group,

10) a 5- or 6-membered heteroaryloxy group,

11) a 4- to 10-membered non-aryl heterocyclyl oxy group,

(wherein each substituent from 5) to 11) is optionally substituted),

12) —SO₂—NR^(e2)R^(f2),

13) —NR^(g2)—CR^(e2)(═NR^(f2)),

14) —NR^(g2)—CR^(e2)(═N—OR^(f2)),

15) —NR^(h2)—C(═NR^(g2))NR^(e2)R^(f2),

16) —NR^(h2)—C(═N—OR²)NR^(e2)R^(f2),

17) —NR^(i2)—C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

18) —NR^(i2)—C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

19) —C(═NR^(e2))R^(f2),

20) —C(═N—OR^(e2))R^(f2),

21) —C(═NR^(h2))—NR^(e2)R^(f2),

22) —C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

23) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

24) —NR^(e2)R^(f2),

25) —NR^(g2)—NR^(e2)R^(f2),

26) —NR^(e2)OR^(f2),

27) —NR^(e2)—C(═O)R^(f2),

28) —C(═O)NR^(e2)R^(f2),

29) —C(═O)NR^(e2)OR^(f2),

30) —C(═O)NR^(g2)—NR^(e2)R^(f2),

31) —C(═O)R^(e2),

32) —C(═O)OR^(e2), and

33) —C(═N—OR^(h2))NR^(e2)R^(f2), and

each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₁₋₄ alkyl group (wherein the alkyl group is optionally substituted),

4) a C₃₋₁₀ alicyclic group (wherein the alicyclic group is optionally substituted),

5) —C(═NR^(e2))R^(f2),

6) —C(═N—OR^(e2))R^(f2),

7) —SO₂—NR^(e2)R^(f2),

8) —C(═NR^(h2))—NR^(e2)R^(f2),

9) —C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

10) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

11) —C(═O)NR^(e2)R^(f2),

12) —C(═O)NR^(e2)OR^(f2),

13) —C(═O)NR^(g2)—NR^(e2)R^(f2),

14) —C(═O)R^(e2), and

15) —C(═N—OR^(h2))NR^(e2)R^(f2).

[Item A25]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A24, wherein R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom,

3) a C₁₋₆ alkyl group,

4) a C₁₋₆ alkoxy group, and

5) a C₁₋₆ alkylthio group,

(wherein each substituent from 3) to 5) is optionally substituted).

[Item A26]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A25, wherein R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom, and

3) an optionally substituted C₁₋₆ alkyl group.

[Item A27]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A26, wherein R¹ and R² are both hydrogen atoms.

[Item A28]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A27, wherein the compounds of formulas (1a) and (1b), the compounds of formulas (3a) and (3b), the compounds of formulas (4a) and (4b), or the compounds of formulas (5a) and (5b) are represented by formulas (6a) and (6b), respectively:

wherein

L³, L⁴, and R⁵ are defined the same as any one of items A1 to A24,

m is an integer 1, 2, or 3,

n is an integer 1, 2, or 3, and

m+n is 2, 3, or 4.

[Item A29]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A28, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

[Item A30]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A29, wherein m is 1 and n is 1.

[Item A31]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A30, wherein R⁵ is 5- or 6-membered aryl or heteroaryl selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) halogen,

4) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), —C(═O)OR^(f2), or a hydroxyl group),

5) a C₁₋₄ alkoxy group

6) —NR^(e2)R^(f2), and

7) —C(═O)OR^(e2), and each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group, and

3) a C₁₋₄ alkyl group,

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), —C(═O)OR^(f2), or a hydroxyl group).

[Item A32]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A31, wherein R^(e2), and R^(f2) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group.

[Item A33]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A32, wherein R^(e2) and R^(f2) are the same or different, each independently a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item A34]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A33, wherein R² and R are hydrogen atoms.

[Item A35]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A24 to A33, wherein R^(6a) is —NR^(e2)R^(f2), and one of R^(e2) and R^(f2) is a hydrogen atom and the other is a C₁₋₄ alkyl group (wherein the alkyl group is optionally substituted with an amino group or a hydroxyl group).

[Item A36]

The compound or the pharmaceutically acceptable salt thereof of item A1, represented by the following compound name or structural formula:

-   7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-acetylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-benzoylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(phenylacetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-phenylalanylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-[(1-D-tyrosylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-[(1-D-valylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   7-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-L-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

or

-   4,4-dihydroxy-8-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

[Item A37]

A salt of the compound of item A36, represented by the following compound name or structural formula:

-   8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

-   8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt

[Item A38]

A compound represented by formula (11):

or a pharmaceutically acceptable salt thereof, wherein

R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), R^(a1), Z, L¹, L², X, R¹, R², R³, and R⁴ are defined the same as the definition according to item A1, and formula (1a) is defined the same as item A1.

[Item A39]

The compound or the pharmaceutically acceptable salt thereof according to item A38, wherein the compound of formula (11) is represented by formula (12):

wherein X, R¹, R², R³, and R⁴ are defined by the same the definition according to item A8. [Item A40]

The compound or the pharmaceutically acceptable salt thereof according to item A38 or A39, wherein the compound of formula (12) is represented by formula (13):

wherein X, Y, ring A, L³, L⁴, R¹, R², R⁴, and R⁵ are defined the same as the definition according to any one of items A10 to A14 and items A16 to A27. [Item A41]

The compound or the pharmaceutically acceptable salt thereof according to item A40, wherein X and R^(G) are hydroxyl groups, R⁴ is a carboxyl group, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle.

[Item A42]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A41, wherein the compound of formula (13) is represented by formula (14):

wherein X, L³, L⁴, m, n, and R⁵ are defined the same as the definition according to item A28. [Item A43]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A42, wherein R^(G) is a hydroxyl group or a thiol group.

[Item A44]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A43, wherein R^(G) is a hydroxyl group.

[Item A45]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A44, wherein X is a hydroxyl group or a C₁₋₆ alkoxy group.

[Item A46]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A45, wherein X is a hydroxyl group.

[Item A47]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A42 to A46, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

[Item A48]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A42 to A47, wherein m is 1, and n is 1.

[Item A49]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A48, wherein

L³ is defined the same as the definition according to item A16 or A17.

[Item A50]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A38 to A49, wherein L⁴ is defined the same as the definition according to any one of items A18 to A20.

[Item A51]

The compound or the pharmaceutically acceptable salt thereof according to item A38, selected from the group consisting of the following compounds:

-   6-[(1-acetylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(methanesulfonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-benzoylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(phenylacetyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-phenylalanylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-tyrosylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-6-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-valylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-6-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-prolylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-L-prolylazetidin-3-yl)oxy]benzoic     acid

-   6-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}benzoic     acid

[Item A52]

A medicament comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51.

[Item A53]

The medicament according to item A52, which is a therapeutic drug or a prophylactic drug for a bacterial infection.

[Item A54]

A β-lactamase inhibiting agent comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51 as an active ingredient.

[Item A55]

A pharmaceutical composition comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51 and a pharmaceutically acceptable carrier.

[Item A56]

The pharmaceutical composition according to item A55, further comprising an additional agent.

[Item A57]

The pharmaceutical composition according to item A56, wherein the additional agent is selected from the group consisting of an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, and an anti-allergic agent.

[Item A58]

The pharmaceutical composition according to item A56 or A57, wherein the additional agent is a 3-lactam agent.

[Item A59]

The pharmaceutical composition according to item A57 or A58, wherein a β-lactam agent, which is the additional agent, is selected from the group consisting of amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, and talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethyl penicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin and flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cefradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicide, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

[Item A60]

The pharmaceutical composition according to item A58 or A59, wherein the β-lactam agent is selected from ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, or panipenem.

[Item A61]

The pharmaceutical composition according to item A58 or A59, wherein the β-lactam agent is selected from aztreonam, tigemonam, BAL30072, SYN2416, or carumonam.

[Item A62]

The pharmaceutical composition according to item A55, characterized in that an additional agent is concomitantly administered.

[Item A63]

The pharmaceutical composition according to item A62, wherein the additional agent is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

[Item A64]

The pharmaceutical composition according to item A62 or A63, wherein the additional agent is a β-lactam agent.

[Item A65]

The pharmaceutical composition according to item A63 or A64, wherein a β-lactam agent, which is the additional agent, is selected from the group consisting of amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, and talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethyl penicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin and flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cefradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicide, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

[Item A66]

The pharmaceutical composition according to item A64 or A65, wherein the β-lactam agent is selected from the group consisting of ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem.

[Item A67]

The pharmaceutical composition according to item A64 or A65, wherein the β-lactam agent is selected from the group consisting of aztreonam, tigemonam, BAL30072, SYN2416, and carumonam.

[Item A68]

The compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51 for treating a bacterial infection.

[Item A69]

The compound or the pharmaceutically acceptable salt thereof according to item A68, wherein the bacterial infection is a bacterial infection in which a bacteria that can have a β-lactamase is involved.

[Item A70]

The compound or the pharmaceutically acceptable salt thereof according to item A68 or A69, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

[Item A71]A medicament comprised of a combination of the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51 and at least one agent selected from the group consisting of therapeutic agents for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, and an odontogenic infection. [Item A72]

A pharmaceutical composition comprising a β-lactam agent, wherein the pharmaceutical composition is administered with the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51.

[Item A73]

A method for treating a bacterial infection, characterized in that a therapeutically effective amount of the compound or the pharmaceutically acceptable salt thereof according to any one of items A1 to A51 is administered to a patient in need thereof.

[Item A74]

The method according to item A73, wherein the bacterial infection is a bacterial infection in which a bacteria that can have a β-lactamase is involved.

[Item A75]

The method according to item A73 or A74, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

[Item A76]

The method according to any one of items A73 to A75, characterized in that an additional agent is concomitantly administered.

The present invention also provides the following.

[Item 1]

A compound represented by formula (1a) or (1b):

or a pharmaceutically acceptable salt thereof, wherein

G is an oxygen atom, a sulfur atom, or —NR^(a1)—,

X is a hydroxyl group, an optionally substituted C₁₋₆ alkoxy group, or —NR^(a2)R^(b1),

R^(a1), R^(a2), and R^(b1) are the same or different, each independently

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl

5) 5- or 6-membered heteroaryl,

6) a 4- to 10-membered non-aryl heterocycle,

7) a C₁₋₆ alkylcarbonyl group,

8) a C₃₋₁₀ alicyclic carbonyl group,

9) a C₆₋₁₀ arylcarbonyl group,

10) a 5- or 6-membered heteroarylcarbonyl group,

11) a C₁₋₆ alkylsulfonyl group,

12) a C₃₋₁₀ alicyclic sulfonyl group,

13) a C₆₋₁₀ arylsulfonyl group,

14) a 5- or 6-membered heteroarylsulfonyl group, or

15) —OR^(c1),

(wherein each substituent from 2) to 14) is optionally substituted),

wherein R^(a2) and R^(b1) together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(c1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle,

(wherein each substituent from 2) to 6) is optionally substituted),

L¹ is a single bond, an oxygen atom, a sulfur atom, —SO—, —SO₂—, —NR^(d)—, —NR^(d)C(═O)—, or —NR^(d)SO₂—,

L² is a single bond or an optionally substituted C₁₋₆ alkylene group,

Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a carboxyl group,

5) a C₃₋₁₀ alicyclic group,

6) C₆₋₁₀ aryl,

7) 5- or 6-membered heteroaryl,

8) a 4- to 10-membered non-aryl heterocycle,

9) a C₁₋₆ alkoxy group,

10) a C₃₋₁₀ alicyclic oxy group,

11) a C₆₋₁₀ aryloxy group,

12) a 5- or 6-membered heteroaryloxy group,

13) a 4- to 10-membered non-aryl heterocyclyl oxy group,

14) a C₁₋₆ alkylthio group,

15) a C₃₋₁₀ alicyclic thio group,

16) a C₁₋₁₀ arylthio group,

17) a 5- or 6-membered heteroarylthio group,

18) a 4- to 10-membered non-aryl heterocyclyl thio group,

(wherein each substituent from 5) to 18) is optionally substituted),

19) —SO₂—NR^(e1)R^(f1),

20) —NR^(e1)—C(═O)OR^(f1),

21) —NR^(g1)—C(═O)NR^(e1)R^(f1),

22) —NR^(e1)—C(═S)R^(f1),

23) —NR^(e1)—C(═S)OR^(f1),

24) —NR^(g1)—C(═S)NR^(e1)R^(f1),

25) —NR^(g1)—CR^(e1)(═NR^(f1)),

26) —NR^(g1)—CR^(e1)(═N—OR^(f1)),

27) —NR^(h1)—C(═NR^(g1))NR^(e1)R^(f1),

28) —NR^(h1)—C(═N—OR^(g1))NR^(e1)R^(f1),

29) —NR^(i1)—C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

30) —NR^(i1)—C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

31) —NR^(e1)—SO—R^(f1),

32) —NR^(g1)—SO₂—NR^(e1)R^(f1),

33) —C(═O)OR^(e1),

34) —C(═S)OR^(e1),

35) —C(═S)NR^(e1)R^(f1),

36) —C(═S)NR^(e1)OR^(f1),

37) —C(═S)NR^(g1)—NR^(e1)R^(f1),

38) —C(═NR^(e1))R^(f1),

39) —C(═N—OR^(e1))R^(f1),

40) —C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

41) —C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

42) —NR^(e1)R^(f1),

43) —NR^(g1)—NR^(e1)R^(f1),

44) —NR^(e1)OR^(f1),

45) —NR^(e1)—C(═O)R^(f1),

46) —C(═O)NR^(e1)R^(f1),

47) —C(═O)NR^(e1)OR^(f1),

48) —C(═O)NR^(g1)—NR^(e1)R^(f1),

49) —C(═O)R^(e1),

50) —C(═NR^(g1))NR^(e1)R^(f1), or

51) —C(═N—OR^(h1))NR^(e1)R^(f1),

one of R¹, R², and R³ is a group represented by formula (2):

wherein

Y is an oxygen atom, a sulfur atom, or —NR^(j)—,

ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle,

L³ is —C(═O)—, —S(═O)—, or —S(═O)₂—,

L⁴ is

1) a single bond,

2) a C₁₋₆ alkylene group,

3) a C₃₋₁₀ cycloalkylene group,

4) a C₆₋₁₀ arylene group,

5) a 5- or 6-membered heteroarylene group,

6) a 4- to 10-membered non-aryl heterocyclylene group, or

7) —C(═N—OR^(h1))—,

(wherein each substituent from 2) to 6) is optionally substituted), and

R⁵ is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) a 4- to 10-membered non-aryl heterocycle,

5) C₆₋₁₀ aryl,

6) 5- or 6-membered heteroaryl,

7) a C₁₋₆ alkylthio group,

(wherein each substituent from 2) to 7) is optionally substituted), or

8) —NR^(e1)OH,

the remaining two (without the structure of formula (2) among R¹, R², and R³) are the same or different, each independently a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted C₁₋₆ alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR^(a3)R^(b2),

R^(d), R^(e1), R^(e2), R^(f1), R^(f2), R^(g1), R^(g2), R^(h1), R^(h2), R^(i1), R^(i2), and R^(j) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₃₋₁₀ alicyclic group, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle,

a combination of R^(e1) and R^(f1) or R^(e2) and R^(f2), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R⁴ is

1) —C(═O)R⁸,

2) —SO₂-L⁶-R⁸,

(wherein R⁸ in 1) and 2) is —NR^(a5)R^(b4), —NR^(a5)-L⁷-B(OR^(m1))₂, —OR^(m1), or an optionally substituted C₁₋₆ alkyl group, and L⁶ is a single bond or —NR^(a6)—),

3) —NR^(a4)R^(b3),

4) —B(OR^(m1))₂,

5) —PO(OR^(m1)) (OR^(m2)),

6) optionally substituted 5-membered heteroaryl,

7) an optionally substituted 5-membered non-aryl heterocycle, or

8) a bioisostere of one of 1) to 7),

(wherein the formulas of 2), 4), 5), and 6) include a carboxylic acid isostere, and 8) may include them in duplicates),

R^(a3), R^(a4), R^(a5), R^(a6), R^(b2), R^(b3), and R^(b4) are the same or different, each independently having the same definition as R^(a1), R^(a2), and R^(b1), wherein a combination of R^(a3) and R^(b2), R^(a4) and R^(b3), or R^(a5) and R^(b4), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(m1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle,

(wherein each substituent from 2) to 6) is optionally substituted),

wherein if R^(m1) is attached to a boron atom via an oxygen atom, two R^(m1), as C₂₋₄ alkylene, together with the boron atom and two oxygen atoms, may form a 5- to 7-membered non-aryl heterocycle (wherein an alkylene moiety is optionally substituted in the non-aryl heterocycle),

R^(m2) is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group, and L⁷ is an optionally substituted C₁₋₃ alkylene group.

[Item 2]

The compound or the pharmaceutically acceptable salt thereof according to item 1, wherein

L¹ is a single bond, a sulfur atom, —NR^(d)C(═O)—, or —NR^(d)SO₂—,

L² is a single bond or an optionally substituted C₁₋₆ alkylene group, and

Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl,

6) a 4- to 10-membered non-aryl heterocycle,

7) —C(═N—OR^(e1))R^(f1), or

8) —NR^(e1)R^(f1).

[Item 3]

The compound or the pharmaceutically acceptable salt thereof according to item 1 or 2, wherein

Z-L²-L¹ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₁₋₆ alkylthio group.

[Item 4]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein Z-L²-L¹ is a hydrogen atom.

[Item 5]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein G is an oxygen atom.

[Item 6]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein X is a hydroxyl group or an optionally substituted C₁₋₆ alkoxy group.

[Item 7]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein X is a hydroxyl group.

[Item 8]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the compounds of formulas (1a) and (1b) are represented by formulas (3a) and (3b), respectively:

wherein X, R¹, R², and R³ are defined the same as any one of the preceding items, and

R⁴ is selected from the group consisting of

1) —COOR^(m1) (wherein R^(m1) is a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₁₀ alicyclic group, C₆₋₁₀ aryl, 5- or 6-membered heteroaryl, or a 4- to 10-membered non-aryl heterocycle, wherein the C₁₋₆ alkyl group, the C₃₋₁₀ alicyclic group, the C₆₋₁₀ aryl, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle are each optionally substituted), and 2) a bioisostere of 1). [Item 9]

The compound or the pharmaceutically acceptable salt thereof according to item 8, wherein R⁴ is

1) —COOH (i.e., a carboxyl group), or

2) a carboxylic acid isostere.

[Item 10]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the compounds of formulas (1a) and (1b) or the compounds of formulas (3a) and (3b) are represented by formulas (4a) and (4b), respectively:

wherein X, R⁴, Y, ring A, L³, L⁴, and R⁵ are defined the same as any one of the preceding items, and

R¹ and R² are the same or different, each independently a hydrogen atom, a halogen atom, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group (wherein the C₁₋₆ alkyl group and the C₁₋₆ alkoxy group are optionally substituted with 1 to 5 halogen atoms).

[Item 11]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle.

[Item 12]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle.

[Item 13]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein Y is an oxygen atom or a sulfur atom.

[Item 14]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein Y is an oxygen atom.

[Item 15]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the compounds of formulas (1a) and (1b), the compounds of formulas (3a) and (3b), or the compounds of formulas (4a) and (4b) are represented by formulas (5a) and (5b), respectively:

wherein ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle. [Item 16]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L³ is —C(═O)— or —S(═O)₂—.

[Item 17]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L³ is —C(═O)—.

[Item 18]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, —C(═N—OR^(h1))—, or an optionally substituted C₁₋₆ alkylene group, wherein R^(h1) is an optionally substituted C₁₋₆ alkyl group.

[Item 19]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom,

3) a C₁₋₆ alkyl group,

4) a C₁₋₆ alkoxy group, and

5) a C₁₋₆ alkylthio group,

(wherein each substituent from 3) to 5) is optionally substituted).

[Item 20]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom, and

3) an optionally substituted C₁₋₆ alkyl group.

[Item 21]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R¹ and R² are both hydrogen atoms.

[Item 22]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the compounds of formulas (1a) and (1b), the compounds of formulas (3a) and (3b), the compounds of formulas (4a) and (4b), or the compounds of formulas (5a) and (5b) are represented by formulas (6a) and (6b), respectively:

wherein L³, L⁴, and R⁵ are defined the same as any one of the preceding items,

m is an integer 1, 2, or 3,

n is an integer 1, 2, or 3, and

m+n is 2, 3, or 4.

[Item 23]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

[Item 24]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein m is 1 and n is 1.

[Item 25]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, or a C₁₋₆ alkylene group optionally substituted with —NR²¹R²² or ═NOR²³, wherein R²¹, R²², and R² are each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted 4- to 10-membered non-aryl heterocyclyl carbonyl group.

[Item 26]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, —CH₂—, —CH(NH₂)—, or —CH(NH₂)—CH₂—, wherein if an amino group is present in L⁴, carbon that attaches to the amino group attaches to L³.

[Item 27]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, —CH₂—, —CMe(NH₂)—, —CH(NHMe)-, —CD(NH₂)— (wherein D represents a heavy hydrogen atom), —CH(NH₂)—, or —CH₂CH₂—.

[Item 28]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, —CH₂—, or —CH(NH₂)—.

[Item 29]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R⁵ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, an optionally substituted C₁₋₆ alkylthio group, or —NR^(e1)OH, wherein R^(e1) is a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item 30]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R⁵ is optionally substituted 5- or 6-membered heteroaryl or optionally substituted C₆₋₁₀ aryl.

[Item 31]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R⁵ is optionally substituted 5- or 6-membered heteroaryl.

[Item 32]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R⁵ is an optionally substituted 4- to 10-membered non-aryl heterocycle.

[Item 33]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is a single bond, and R⁵ is —NR^(e1)OH, wherein R^(e1) is a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item 34]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is

1) —(CH₂)_(p)—CR¹⁰(NHR¹¹)—,

2) —(CH₂)_(q)—CR¹²R¹³, or

3) —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CR¹²R¹³— (wherein p and q are independently 0 or 1),

R¹⁰ is

1) a hydrogen atom,

2) a carboxyl group, or

3) —C(═O)NR^(10a)R^(10b),

R¹ is

1) a hydrogen atom,

2) —C(═O)R^(11a), or

3) an optionally substituted 5- or 6-membered non-aryl heterocyclyl carbonyl group,

wherein if R¹⁰ is —C(═O)NR^(10a)R^(10b), R^(10b) and R¹¹ together may form —CH₂CH₂—,

R¹² is

1) a hydrogen atom, or

2) an optionally substituted C₁₋₄ alkyl group,

R¹³ is

1) a hydrogen atom,

2) a hydroxyl group,

3) an optionally substituted C₁₋₄ alkyl group,

4) a sulfanyl group,

5) a carboxyl group,

6) an optionally substituted C₁₋₄ alkylthio group,

7) —NR^(13a)R^(13b),

8) —NR^(13a)—C(═O)R^(13b),

9) an optionally substituted 5- or 6-membered non-aryl heterocyclyl carbonylamino group,

10) —NR^(13a)—C(═O)NR^(13b)R^(13c),

11) —C(═O)NR^(13a)R^(13b),

12) —C(═O)NR^(13a)OR^(13b),

13) —S(═O)₂—R^(13a),

14) —S(═O)₂—NR^(13a)R^(13b),

15) —C(═O)NR^(13a)—S(═O)₂—R^(13b) or

16) —C(═O)NR^(3a)—S(═O)₂—NR^(13b)R^(13c), and

R^(10a), R^(10b), R^(11a), R^(13a), R^(13b), and R^(13c) are each independently a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

[Item 35]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein R⁵ is a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

[Item 36]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 31, wherein

R⁵ is selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a nitro group,

5) halogen,

6) a C₁₋₄ alkyl group,

7) a C₃₋₁₀ alicyclic group,

8) a C₁₋₄ alkoxy group,

9) a C₃₋₁₀ alicyclic oxy group,

10) a C₆₋₁₀ aryloxy group,

11) a 5- or 6-membered heteroaryloxy group,

12) a 4- to 10-membered non-aryl heterocyclyl oxy group,

(wherein each substituent from 6) to 12) is optionally substituted),

13) —SO₂—NR^(e2)R^(f2),

14) —NR^(g2)—CR^(e2) (═NR^(f2)),

15) —NR^(g2)—CR^(e2)(═N—OR),

16) —NR^(h2)—C(═NR^(g2))NR^(e2)R^(f2),

17) —NR^(h2)—C(═N—OR^(g2))NR^(e2)R^(f2),

18) —NR^(i2)—C(═NR^(h2))NR^(g1)—NR^(e2)R^(f2),

19) —NR^(i2)—C(═N—OR^(h2))NR^(g1)—NR^(e2)R^(f2),

20) —C(═NR^(e2))R^(f2),

21) —C(═N—OR^(e2))R^(f2),

22) —C(═NR^(h2))—NR^(e2)R^(f2),

23) —C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

24) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

25) —NR^(e2)R^(f2),

26) —NR^(g2)—NR^(e2)R^(f2),

27) —NR^(e2)OR^(f2),

28) —NR^(e2)—C(═O)R^(f2),

29) —C(═O)NR^(e2)R^(f2),

30) —C(═O)NR^(e2)OR^(f2),

31) —C(═O)NR^(g2)—NR^(e2)R^(f2),

32) —C(═O)R^(e2),

33) —C(═O)OR^(e2), and

34) —C(═N—OR^(h2))NR^(e2)R^(f2), and

each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted)

4) a C₃₋₁₀ alicyclic group

(wherein the alicyclic group is optionally substituted),

5) —C(═NR^(e2))R^(f2),

6) —C(═N—OR^(e2))R^(f2),

7) —SO₂—NR^(e2)R^(f2),

8) —C(═NR^(h2))—NR^(e2)R^(f2),

9) —C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

10) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

11) —C(═O)NR^(e2)R^(f2),

12) —C(═O)NR^(e2)OR^(f2),

13) —C(═O)NR^(g2)—NR^(e2)R^(f2),

14) —C(═O)R², and

15) —C(═N—OR^(h2))NR^(e2)R^(f2).

[Item 37]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 31 and 36, wherein R⁵ is 5- or 6-membered aryl or heteroaryl selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) halogen,

4) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), a 5- or 6-membered non-aryl heterocycle, —C(═O)OR^(f2), or a hydroxyl group),

5) a C₁₋₄ alkoxy group

6) —NR^(e2)R^(f2), and

7) —C(═O)OR^(e2), and

each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group, and

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), —C(═O)NR^(e2)R^(f2), —C(═O)OR^(f2), or a hydroxyl group).

[Item 38]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 31, 36, and 37, wherein R^(e2) and R^(f2) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group.

[Item 39]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 31 and 36 to 38, wherein R^(e2) and R^(f2) are the same or different, each independently a hydrogen atom or an optionally substituted C₁₋₆ alkyl group.

[Item 40]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 31 and 36 to 39, wherein R^(e2) and R^(f2) are hydrogen atoms.

[Item 41]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 36 to 39, wherein R^(6a) is —NR^(e2)R^(f2), and one of R^(e2) and R^(f2) is a hydrogen atom and the other is a C₁₋₄ alkyl group (wherein the alkyl group is optionally substituted with an amino group or a hydroxyl group).

[Item 42]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 29 and 32, wherein R⁵ is a 4- to 6-membered non-aryl heterocycle selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(7a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) halogen,

5) a C₁₋₄ alkyl group,

6) a C₃₋₁₀ alicyclic group,

7) a C₁₋₄ alkoxy group,

8) a C₃₋₁₀ alicyclic oxy group,

9) a C₆₋₁₀ aryloxy group,

10) a 5- or 6-membered heteroaryloxy group,

11) a 4- to 10-membered non-aryl heterocyclyl oxy group,

(wherein each substituent from 5) to 11) is optionally substituted),

12) —SO₂—NR^(e3)R^(f3),

13) —NR^(g2)—CR^(e3)(═NR^(f3)),

14) —NR^(g2)—CR^(e3)(═N—OR^(f3)),

15) —NR^(h2)—C(═NR^(g2))NR^(e3)R^(f3),

16) —NR^(h2)—C(═N—OR^(g2))NR^(e3)R^(f3),

17) —NR^(i2)—C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

18) —NR^(i2)—C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

19) —C(═NR^(e3))R^(f3),

20) —C(═N—OR^(e3))R^(f3),

21) —C(═NR^(h2))—NR^(e3)R^(f3),

22) —C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

23) —C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

24) —NR^(e3)R^(f3),

25) —NR^(g2)—NR^(e3)R^(f3),

26) —NR^(e3)OR^(f3),

27) —NR^(e3)—C(═)R^(f3),

28) —C(═O)NR^(e3)R^(f3),

29) —C(═O)NR^(e3)OR^(f3),

30) —C(═O)NR²—NR^(e3)R^(f3),

31) —C(═O)R^(e3),

32) —C(═O)OR^(e3), and

33) —C(═N—OR^(h2))NR^(e3)R^(f3),

each R^(7b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted),

4) a C₃₋₁₀ alicyclic group

(wherein the alicyclic group is optionally substituted),

5) —C(═NR^(e3))R^(f3),

6) —C(═N—OR^(e3))R,

7) —SO₂—NR^(e3)R^(f3),

8) —C(═NR^(h2))—NR^(e3)R^(f3),

9) —C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

10) —C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

11) —C(═O)NR^(e3)R^(f3),

12) —C(═O)NR^(e3)OR^(f3),

13) —C(═O)NR^(g2)—NR^(e3)R^(f3),

14) —C(═O)R^(e3), and

15) —C(═N—OR^(h2))NR^(e3)R^(f3), and

R^(e3) and R^(f3) are defined the same as R^(e2) and R^(f2) according to item 1.

[Item 43]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 29, 32, and 42, wherein

R⁵ is a 4- to 6-membered non-aryl heterocycle selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(7a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) halogen,

4) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e3)R^(f3), a 5- or 6-membered non-aryl heterocycle, —C(═O)OR^(f3), or a hydroxyl group),

5) a C₁₋₄ alkoxy group

6) —NR^(e3)R^(f3),

7) —C(═O)OR^(e3),

8) C₆₋₁₀ aryl, and

9) —C(═O)NR^(e3)R^(f3),

each R^(7b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group, and

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e3)R^(f3), —C(═O)OR^(f3), or a hydroxyl group), and

R^(e3) and R^(f3) are defined the same as R^(e2) and R^(f2) according to any one of items 38 to 40.

[Item 44]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CH(NH₂) —CHR¹³—, wherein carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom, and

R¹ is

1) —NH—C(═O)CH₃,

2) —NH—C(═O)NH₂,

3) —NH—C(═O)CH(NH₂)—CH₂C(═O)NH₂,

4) —NH—C(═O)CH₂—NH₂,

5) —NH—C(═O)CH(NH₂)—CH₂OH, or

6) a pyrrolidin-2-ylcarbonylamino group.

[Item 45]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is —CH(NH₂) —CR¹²R¹³—, wherein carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom or methyl,

R¹² is a hydrogen atom or methyl, and

R¹³ is a benzylthio group or a sulfanyl group.

[Item 46]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein L⁴ is —CH(NH₂)—(CH₂)_(q)—CHR¹³—, wherein q is 0 or 1, and carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom, and

R¹³ is

1) a carboxyl group,

2) —C(═O)NH₂,

3) —C(═O)NH(CH₃),

4) —C(═O)N(CH₃),

5) —C(═O)NH—(CH₂)₂—OH,

6) —C(═O)NH—(CH₂)₂—NH₂,

7) —C(═O)NH—S(═O)₂—CH₃,

8) —C(═O)NHOH,

9) —S(═O)₂—NH₂,

10) —S(═O)₂—CH₃, or

11) a hydroxyl group.

[Item 47]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CH(NHR¹¹)—CH₂—, wherein carbon that attaches to the NHR¹¹ attaches to L³,

R⁵ is hydrogen, and

R¹¹ is

1) —C(═O)CH(NH₂)—CH₂C(═O)NH₂,

2) —C(═O)CH₂—NH₂,

3) —C(═O)CH(CH₃)—NH₂,

4) —C(═O)CH(NH₂)—CH₂OH, or

5) pyrrolidin-2-ylcarbonyl.

[Item 48]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CH(NHR¹¹)—CH(COOH)—, wherein carbon that attaches to the NHR¹¹ attaches to L³,

R⁵ is hydrogen, and

R¹¹ is

1) —C(═O)CH(NH₂)—CH₂C(═O)NH₂,

2) —C(═O)CH₂—NH₂,

3) —C(═O)CH(CH₃)—NH₂,

4) —C(═O)CH(NH₂)—CH₂OH, or

5) pyrrolidin-2-ylcarbonyl.

[Item 49]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CHR¹³— or —CH₂—CHR¹³—,

R⁵ is hydrogen, and

R¹³ is —C(═O)NH₂ or —C(═O)NHOH.

[Item 50]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CH₂—CR¹⁰(NH₂)—, wherein the CH₂ attaches to L³,

R⁵ is hydrogen, and

R¹⁰ is a carboxy group or —C(═O)NH₂.

[Item 51]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CHR¹³— or —CHR¹³—(CH₂)_(q)—CR¹⁰(NHR¹¹)—(CH)_(p)—, wherein q is 0 or 1,

R⁵ is hydrogen,

(1) if L⁴ is —CHR¹³—(CH₂)_(q)—CR¹⁰(NHR¹¹)—(CH₂)_(p)—, carbon of the —CHR¹³— group attaches to L³,

p is 0,

R¹⁰ is a hydrogen atom, a carboxyl group, or —C(═O)NHR^(10b),

R¹¹ is a hydrogen atom,

R^(10b) is a hydrogen atom,

wherein if R¹⁰ is —C(═O)NHR^(10b), R^(10b) and R¹¹ together may form —CH₂CH₂—, and

R¹³ is a hydrogen atom, and

(2) if L⁴ is —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CHR¹³—, carbon of the —(CH₂)_(p)— group attaches to L³,

p is 1,

R¹⁰ and R¹¹ are both hydrogen atoms,

R¹³ is a carboxyl group or —C(═O)NR^(13a)R^(13b), and

R^(13a) and R^(13b) are each independently a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

[Item 52]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein

L⁴ is —CR¹²(NH₂)—,

R¹² is a hydrogen atom or a methyl group, and

R⁵ is a C₁₋₄ alkyl group optionally substituted with a hydroxyl group.

[Item 53]

The compound or the pharmaceutically acceptable salt thereof according to item 1, represented by the following compound name or structural formula:

-   7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-acetylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

2-hydroxy-7-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

-   4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-benzoylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(phenylacetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-phenylalanylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-[(1-D-tyrosylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-[(1-D-valylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   7-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-L-prolylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

[Item 54]

The compound or the pharmaceutically acceptable salt thereof of item 1, represented by the following compound name or structural formula:

-   7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[2-amino-2-(1H-imidazol-4-yl)(²H)ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[2-amino-2-(1H-imidazol-4-yl)     (²H)ethanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4′-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1-oxo-1λ⁵-pyridine-2-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1-oxo-1λ⁵-pyridine-2-sulfonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

4,4-dihydroxy-8-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

-   2-hydroxy-7-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-({4[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   7-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-D-cysteinylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   7-[(1-D-cysteinylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-L-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-L-asparaginylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   7-[(1-D-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-D-asparaginylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-D-glutaminylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-D-glutaminylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-L-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-L-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   7-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

-   2-hydroxy-7-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4S)-carbamoyl-L-propyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-S-carboxylic     acid

-   4,4-dihydroxy-8-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(1,1-dioxo-1λ²-thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(1,1-dioxo-1λ⁶-thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine

-   N-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine

-   N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-aspartamide

-   N¹-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide

-   N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide

-   N-[(2R)-1-{3-[(7-carboxy-4,4-hydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-trien-8-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide

-   7-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{1-[(3S)-amino-3-amino-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4R)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   7-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   8-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-D-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-D-threonylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid

-   2-hydroxy-7-[(1-L-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid

-   4,4-dihydroxy-8-[(1-L-threonylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic

[Item 55]

A compound represented by formula (11):

or a pharmaceutically acceptable salt thereof, wherein R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), R^(a1), Z, L¹, L², X, R¹, R², R³, and R⁴ are defined the same as the definition according to item 1, and formula (1a) is defined the same as item 1. [Item 56]

The compound or the pharmaceutically acceptable salt thereof according to item 55, wherein the compound of formula (11) is represented by formula (12):

wherein X, R¹, R², R³, and R⁴ are defined the same as the definition according to any one of the preceding items. [Item 57]

The compound or the pharmaceutically acceptable salt thereof according to item 55 or 56, wherein the compound of formula (12) is represented by formula (13):

wherein X, Y, ring A, L³, L⁴, R¹, R², R⁴, and R⁵ are defined the same as the definition according to any one of the preceding items. [Item 58]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 57, wherein X and R^(G) are hydroxyl groups, R⁴ is a carboxyl group, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle.

[Item 59]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 58, wherein the compound of formula (13) is represented by formula (14):

wherein X, L³, L⁴, m, n, and R⁵ are defined the same as the definition according to any one of the preceding items. [Item 60]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 59, wherein R^(G) is a hydroxyl group or a thiol group.

[Item 61]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 60, wherein R^(G) is a hydroxyl group.

[Item 62]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 61, wherein X is a hydroxyl group or a C₁₋₆ alkoxy group.

[Item 63]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 62, wherein X is a hydroxyl group.

[Item 64]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 63, wherein m is 1 or 2, n is 1 or 2, and m+n is 2 or 3.

[Item 65]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 64, wherein m is 1, and n is 1.

[Item 66]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 65, wherein L³ is defined the same as the definition according to any one of the preceding items.

[Item 67]

The compound or the pharmaceutically acceptable salt thereof according to any one of items 55 to 66, wherein L⁴ and R⁵ are defined the same as the definitions according to any one of the preceding items.

[Item 68]

The compound or the pharmaceutically acceptable salt thereof according to item 55, selected from the group consisting of the following compounds:

-   6-[(1-acetylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(methanesulfonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-benzoylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(phenylacetyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-phenylalanylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-tyrosylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-6-[(1-D-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-valylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-6-[(1-L-histidylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-prolylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-L-prolylazetidin-3-yl)oxy]benzoic     acid

-   6-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}benzoic     acid

[Item 69]

The compound or the pharmaceutically acceptable salt thereof according to item 55, selected from the group consisting of the following compounds:

-   6-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(4H-1,2,4-triazole-3-sulfonyl)-azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[2-amino-2-(1H-imidazol-4-yl)(²H)ethanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-oxo-1λ⁵-pyridine-2-sulfonyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-f{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl)acetyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic

-   6-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-D-cysteinylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}benzoic     acid

-   6-({1-[(2S)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-L-asparaginylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-[(1-D-asparaginylazetidin-3-yl)oxy]-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-serylazetidin-3-yl)oxy]benzoic     acid

-   6-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-D-glutaminylazetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   6-{[1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-L-serylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(1-methyl-L-prolyl)_azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-({1-[(1,1-dioxo-1λ⁶-thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   6-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   N-[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine

-   N¹-[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide

-   N-[(2R)-1-{3-[4-(2-boronoethyl)-2-carboxy-3-hydroxyphenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide

-   6-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   3-(2-boronoethyl)-6-({1-[(dimethylamino)(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)benzoic     acid

-   6-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   6-({1-[(4R)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-2-hydroxybenzoic     acid

-   6-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   6-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-3-(2-boronoethyl)-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-6-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxybenzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-D-threonylazetidin-3-yl)oxy]benzoic     acid

-   3-(2-boronoethyl)-2-hydroxy-6-[(1-L-threonylazetidin-3-yl)oxy]benzoic     acid

[Item 70]

A medicament comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 69.

[Item 71]

The medicament according to item 70, which is a therapeutic drug or a prophylactic drug for a bacterial infection.

[Item 72]

A β-lactamase inhibiting agent comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 69 as an active ingredient.

[Item 73]

A pharmaceutical composition comprising the compound or the pharmaceutically acceptable salt thereof according to any one of items 1 to 69 and a pharmaceutically acceptable carrier.

[Item 74]

The pharmaceutical composition according to item 73, further comprising an additional agent.

[Item 75]

The pharmaceutical composition according to item 74, wherein the additional agent is selected from the group consisting of an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, and an anti-allergic agent.

[Item 76]

The pharmaceutical composition according to item 74 or 75, wherein the additional agent is a f-lactam agent.

[Item 77]

The pharmaceutical composition according to item 75 or 76, wherein a β-lactam agent, which is the additional agent, is selected from the group consisting of amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, and talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethyl penicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin and flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cefradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicide, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

[Item 78]

The pharmaceutical composition according to item 76 or 77, wherein the β-lactam agent is selected from ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, or panipenem.

[Item 79]

The pharmaceutical composition according to item 76 or 77, wherein the β-lactam agent is selected from aztreonam, tigemonam, BAL30072, SYN2416, or carumonam.

[Item 80]

The pharmaceutical composition according to item 73, characterized in that an additional agent is concomitantly administered.

[Item 81]

The pharmaceutical composition according to item 80, wherein the additional agent is selected from an antibacterial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent.

[Item 82]

The pharmaceutical composition according to item 80 or 81, wherein the additional agent is a β-lactam agent.

[Item 83]

The pharmaceutical composition according to item 81 or 82, wherein a β-lactam agent, which is the additional agent, is selected from the group consisting of amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, and talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethyl penicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin and flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cefradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicide, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442.

[Item 84]

The pharmaceutical composition according to item 82 or 83, wherein the β-lactam agent is selected from the group consisting of ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem.

[Item 85]

The pharmaceutical composition according to item 82 or 83, wherein the @3-lactam agent is selected from the group consisting of aztreonam, tigemonam, BAL30072, SYN2416, and carumonam.

[Item 86]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items for treating a bacterial infection.

[Item 87]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the bacterial infection is a bacterial infection in which a bacteria that can have a β-lactamase is involved.

[Item 88]

The compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

[Item 89]

A medicament comprised of a combination of the compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items and at least one agent selected from the group consisting of therapeutic agents for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, and an odontogenic infection.

[Item 90]

A pharmaceutical composition comprising a β-lactam agent, wherein the pharmaceutical composition is administered with the compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items.

[Item 91]

A method for treating a bacterial infection, characterized in that a therapeutically effective amount of the compound or the pharmaceutically acceptable salt thereof according to any one of the preceding items is administered to a patient in need thereof.

[Item 92]

The method according to any one of the preceding items, wherein the bacterial infection is a bacterial infection in which a bacteria that can have a β-lactamase is involved.

[Item 93]

The method according to any one of the preceding items, wherein the bacterial infection is sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

[Item 94]

The method of any one of the preceding items, characterized in that an additional agent is concomitantly administered.

The present invention is intended so that one or more of the features described above can be provided not only as the explicitly disclosed combinations, but also as other combinations thereof. Additional embodiments and advantages of the invention are recognized by those skilled in the art by reading and understanding the following detailed description as needed.

Advantageous Effects of Invention

The compound of the invention has excellent inhibitory action against serine-β-lactamase with a serine residue at the center of enzymatic activity. A better embodiment of the compound of the invention is expected to have a broad β-lactamase inhibitory action or metallo-β-lactamase inhibitory action with zinc (Zn²⁺) at the center of enzymatic activity against multiple types of β-lactamases. Therefore, the compound of the invention is useful alone or in concomitant use with a β-lactam agent as a therapeutic agent and/or prophylactic agent for a bacterial infection in which a bacteria that can have a β-lactamase is involved, i.e., sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

DESCRIPTION OF EMBODIMENTS

The present invention is described hereinafter in more detail.

Throughout the entire specification, a singular expression should be understood as encompassing the concept thereof in the plural form, unless specifically noted otherwise. Thus, singular articles (e.g., “a”, “an”, “the”, and the like in the case of English) should also be understood as encompassing the concept thereof in the plural form, unless specifically noted otherwise. The terms used herein should also be understood as being used in the meaning that is commonly used in the art, unless specifically noted otherwise. Thus, unless defined otherwise, all terminologies and scientific technical terms that are used herein have the same meaning as the general understanding of those skilled in the art to which the present invention pertains. In case of a contradiction, the present specification (including the definitions) takes precedence.

The terms and the general technologies that are used herein are first described.

Unless specifically noted otherwise, the term “group” refers to a monovalent group. Examples of groups that are not a monovalent group include alkylene groups (divalent). The term “group” may also be omitted in the following descriptions of substituents or the like.

Unless specifically limited, the number of substituents when defined as “optionally substituted” or “substituted” is not particularly limited herein, as long as a substitution is possible. The number of substituents is one or multiple substituents. Moreover, unless indicated otherwise, the description for each substituent is also applicable when the substituent is a part of or a substituent of another group.

A substituent in “optionally substituted” is selected from substituent group a that consists of the following. The substitution is optionally substituted with 1 to 5 of the same or different substituents. While not particularly limited by the type of substituent, if an atom to which the substituent attaches is an oxygen atom, a nitrogen atom, or a sulfur atom, the substituent is limited to the following substituents that attaches to a carbon atom.

Substituent group a includes

1) a halogen atom

2) a hydroxyl group

3) a carboxyl group

4) a cyano group

5) a sulfanyl group,

6) a nitro group,

7) a C₁₋₆ alkyl group

8) a C₂₋₆ alkenyl group

9) a C₂₋₆ alkynyl group

10) a C₁₋₆ alkoxy group

11) a C₁₋₆ alkylthio group

12) a C₁₋₆ alkylcarbonyl group

13) a C₁₋₆ alkylsulfonyl group

(wherein each substituent from 7) to 13) is optionally substituent with 1 to 5 of the same or different sub substituents selected from substituent group β)

14) a C₃₋₁₀ alicyclic group

15) a C₃₋₁₀ alicyclic oxy group

16) a C₆₋₁₀ aryloxy group

17) a 5- or 6-membered heteroaryloxy group

18) a 4- to 10-membered non-aryl heterocyclyl oxy group

19) a C₃₋₁₀ alicyclic thio group

20) a C₆₋₁₀ arylthio group

21) a 5- or 6-membered heteroarylthio group

22) a 4- to 10-membered non-aryl heterocyclyl thio group

23) C₆₋₁₀ aryl

24) 5- or 6-membered heteroaryl

25) a 4- to 10-membered non-aryl heterocycle

26) a C₃₋₁₀ alicyclic carbonyl group

27) a C₆₋₁₀ arylcarbonyl group

28) a 5- or 6-membered heteroarylcarbonyl group

29) a 4- to 10-membered non-aryl heterocyclyl carbonyl group

30) a 4- to 10-membered non-aryl heterocyclyl carbonylamino group

31) a C₃₋₁₀ alicyclic sulfonyl group

32) a C₆₋₁₀ arylsulfonyl group

33) a 5- or 6-membered heteroarylsulfonyl group

34) a 4- to 10-membered non-aryl heterocyclyl sulfonyl group

(wherein each substituent from 14) to 34) is optionally substituted with 1 to 5 of substituent group β or 1) a C₁₋₆ alkyl group)

35) —NR^(10a)R^(11a)

36) —SO₂—R^(10b)

37) —SO₂—NR^(10b)R^(11b)

38) —NR^(10c)—CC(═O)R^(11c)

39) —NR^(10d)—C(═O)OR^(11d)

40) —NR^(12a)—C(═O)NR^(10e)R^(11e)

41) —NR^(10f)—C(═S)R^(11f)

42) —NR^(10g)—C(═S)OR^(11g),

43) —NR^(12b)—C(═S)NR^(10h)R^(11h)

44) —NR^(10i)—SO₂—R^(11i)

45) —NR^(12c)—SO₂—NR^(10j)R^(11j)

46) —C(═O)OR^(10k)

47) —C(═O)NR^(10l)R^(11k)

48) —C(═O)NR^(10m)OR^(11l)

49) —C(═O)NR^(12d)—NR^(10n)R^(11m)

50) —C(═S)OR^(10o)

51) —C(═S)NR^(10p)R^(11n)

52) —C(═S)NR^(10q)OR^(10o)

53) —C(═S)NR^(12e)—NR^(10r)R^(11p)

54) —C(═NR^(13a))R^(10s)

55) —C(═NR^(13b))CHO

56) —C(═NR^(13c))NR^(10t)R^(11q)

57) —C(═NR^(13d))NR^(12f)—NR^(10u)R^(11r)

58) —NR^(17c)—C(═NR^(13e))R^(17d)

59) —NR^(12g)—C(═NR^(13f))—NR^(12h)—NR^(10v)R^(11s)

60) —NR¹⁴—C(═NR^(13f))—NR^(12h)—NR^(10w)R^(11t)

61) —OC(═O)R^(10x)

62) —OC(═O)OR^(10y)

63) —OC(═O)NR^(10z1)R^(11u)

64) —NR^(12i)—NR^(10z2)R^(11v)

65) —NR^(10z3)OR^(11w)

66) —C(═N—OR^(13a))R^(10s)

67) —C(═N—OR^(13b))CHO

68) —C(═N—OR^(13c))NR^(10t)R^(11q)

69) —C(═N—OR^(13d))NR^(12f)—NR^(10u)R^(11r)

70) —C(═O)NR^(12j)—S(═O)₂—R^(10a1) and

71) —C(═O)NR^(12k)—S(═O)₂—NR^(10a2)R^(11x),

substituent group p is a group consisting of

1) a halogen atom,

2) a hydroxyl group,

3) a carboxyl group,

4) a cyano group,

5) a C₃₋₁₀ alicyclic group,

6) a C₁₋₆ alkoxy group,

7) a C₃₋₁₀ alicyclic oxy group,

8) a C₁₋₆ alkylthio group,

9) a 5- or 6-membered heteroarylthio group,

10) C₆₋₁₀ aryl,

11) 5- or 6-membered heteroaryl,

12) a 4- to 10-membered non-aryl heterocycle,

13) a C₁₋₆ alkylcarbonyl group,

14) a C₃₋₁₀ alicyclic carbonyl group,

15) a C₆₋₁₀ arylcarbonyl group,

16) a 5- or 6-membered heteroarylcarbonyl group,

17) a 4- to 10-membered non-aryl heterocyclyl carbonyl group,

18) —NR^(15a)R^(16a),

19) —SO₂—NR^(15b)R^(16b),

20) —NR^(15c)—C(═O)R^(16c)

21) —NR^(17a)—C(═O)NR^(15d)R^(16d),

22) —C(═O)NR^(15e)R^(16e),

23) —C(═NR^(13g))R^(15f),

24) —C(═NR^(13h))NR^(15g)R^(16f)

25) —NR^(16g)—C(═NR^(13i))R^(15h)

26) —NR^(17b)—C(═NR^(13j))—NR^(15i)R^(16h)

27) —C(═N—OR^(13g))R^(15f), and

28) —C(═N—OR^(13h))NR^(15g)R^(16f)

(wherein each substituent from 5) to 17) in substituent group β is optionally substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a carboxyl group, and —NR^(18a)R^(18b)),

R^(13a), R^(13b), R^(13c), R^(13d), R^(13e), R^(13f), R^(13f), R^(13g), R^(13h), R^(13i), R^(13j), and R^(13k) are the same or different, each independently a hydrogen atom, a hydroxyl group, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10f), R^(10g), R^(10h), R^(10i), R^(10j), R^(10k), R^(10l), R^(10m), R^(10n), R^(10o), R^(10p), R^(10q), R^(10r), R^(10s), R^(10t), R^(10u), R^(10v), R^(10w), R^(10x), R^(10y), R^(10a1), R^(10a2), R^(10z1), R^(10z2), R^(10z3), R^(11a), R^(11b), R^(11c), R^(11d), R^(11e), R^(11f), R^(11g), R^(11h), R^(11i), R^(11j), R^(11k), R^(11l), R^(11m), R^(11n), R^(11o), R^(11p), R^(11q), R^(11r), R^(11s), R^(11t), R^(11u), R^(11v), R^(11w), R^(11x), R^(12a), R^(12b), R^(12c), R^(12d), R^(12e), R^(12f), R^(12g), R^(12h), R^(12i), R^(12j), R^(12k), R¹⁴, R^(15a), R^(15b), R^(15c), R^(15d), R^(16h), R^(17a), R^(17b), R^(17c), and R^(17d) are the same or different, each independently a hydrogen atom, a 5- or 6-membered non-aryl heterocycle, or a C₁₋₆ alkyl group (wherein the 5- or 6-membered non-aryl heterocycle and the C₁₋₆ alkyl group are optionally substituted with 1 to 3 of the same or different substituents, each independently selected from the group consisting of a hydroxyl group, a cyano group, a C₁₋₆ alkoxy group, —NR^(18a)R^(18b) a carboxyl group, and —C(═O)NR^(18c)R^(18d)), and

R^(18a), R^(18b), R^(18c), and R^(18d) are the same or different, each independently a hydrogen atom or a C₁₋₆ alkyl group.

Preferred examples of substituents in “optionally substituted” include the following substituents.

Preferred substituent group a includes

1) a halogen atom

2) a hydroxyl group

3) a carboxyl group

4) a cyano group

5) a C₁₋₆ alkyl group

6) a C₁₋₆ alkoxy group

7) a C₁₋₆ alkylthio group

8) a C₁₋₆ alkylcarbonyl group

(wherein each substituent from 5) to 8) is optionally substituted with 1 to 5 of the same or different substituents selected from substituent group 3)

9) a C₃₋₁₀ alicyclic group

10) a C₃₋₁₀ alicyclic oxy group

11) a C₆₋₁₀ aryloxy group

12) a 5- or 6-membered heteroaryloxy group

13) a 4- to 10-membered non-aryl heterocyclyl oxy group

14) a C₃₋₁₀ alicyclic thio group

15) a C₆₋₁₀ arylthio group

16) a 5- or 6-membered heteroarylthio group

17) a 4- to 10-membered non-aryl heterocyclyl thio group

18) C₆₋₁₀ aryl

19) 5- or 6-membered heteroaryl

20) a 4- to 10-membered non-aryl heterocycle

21) a C₃₋₁₀ alicyclic carbonyl group

22) a C₆₋₁₀ arylcarbonyl group

23) a 5- or 6-membered heteroarylcarbonyl group

24) a 4- to 10-membered non-aryl heterocyclyl carbonyl group

(wherein each substituent from 9) to 24) is optionally substituted with 1 to 5 of substituent group (3 or 1) a C₁₋₆ alkyl group)

25) —NR^(10a)R^(11a)

26) —SO₂—NR^(10b)R^(11b)

27) —NR^(10c)—C(═O)R^(11c)

28) —NR^(12a)—C(═O)NR^(10d)R^(11d)

29) —NR^(10e)—SO₂—R^(11e)

30) —NR^(12b)—SO₂—NR^(10f)R^(11f)

31) —C(═O)NR^(10g)R^(11g)

32) —C(═NR^(13a))R^(10h)

33) —C(═NR^(13b))NR^(10i)R^(11h)

34) —NR^(11f)—C(═NR^(13c))R^(10g)

35) —NR^(12c)—C(═NR^(13d))—NR^(10j)R^(11i)

36) —C(═N—OR^(13a))R^(10h), and

37) —C(═N—OR^(13b))NR^(10i)R^(11h),

substituent group β is preferably selected from the group consisting of

1) a halogen atom

2) a hydroxyl group

3) a cyano group

4) a C₃₋₁₀ alicyclic group

5) a C₁₋₆ alkoxy group

6) a C₁₋₆ alkylthio group

7) a 5- or 6-membered heteroarylthio group

8) 5- or 6-membered heteroaryl

9) a 4- to 10-membered non-aryl heterocycle

10) a C₁₋₆ alkylcarbonyl group

11) a C₃₋₁₀ alicyclic carbonyl group

12) a C₆₋₁₀ arylcarbonyl group

13) a 5- or 6-membered heteroarylcarbonyl group

14) a 4- to 10-membered non-aryl heterocyclyl carbonyl group

15) —NR^(15a)R^(16a)

16) —NR^(15b)—C(═O)R^(16b)

17) —NR^(17a)—C(═O)NR^(15c)R^(16c)

18) —C(═O)NR^(15d)R^(16d)

19) —C(═NR^(13e))R^(15e)

20) —C(═NR^(13f))NR^(15f)R^(16e)

21) —NR^(16f)—C(═NR^(13g))R^(15g)

22) —NR^(17b)—C(═NR^(13h))—NR^(15h)R^(16g)

23) —C(═N—OR^(13e))R^(15e) and

24) —C(═N—OR^(13f))NR^(15f)R^(16e)

(wherein each substituent from 4) to 14) in substituent group β is optionally substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a hydroxyl group, a cyano group, a carboxyl group, and —NR^(18a)R^(18b)),

R^(13a), R^(13b), R^(13c), R^(13d), R^(13e), R^(13f), R^(13g), and R^(13h) are the same or different, each independently a hydrogen atom, a hydroxyl group, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10f), R^(10g), R^(10h), R^(10i), R^(10j), R^(11a), R^(11b), R^(11c), R^(11d), R^(11e), R^(11f), R^(11g), R^(11h), R^(11i), R^(12a), R^(12b), R^(12c), R^(15a), R^(15b), R^(15c), R^(15d), R^(15e), R^(15f), R^(15g), R^(15h), R^(16a), R^(16b), R^(16c), R^(16d), R^(16e), R^(16f), R^(16g), R^(17a), and R^(17b) are the same or different, each independently a hydrogen atom or a C₁₋₆ alkyl group (wherein the group is optionally substituted with 1 to 3 of the same or different substituents selected from a hydroxyl group, a cyano group, C₁₋₆ alkoxy group, and —NR^(18a)R^(18b)), and

R^(18a) and R^(18b) are the same or different, each independently a hydrogen atom or a C₁₋₆ alkyl group.

More preferred examples of substituents in “optionally substituted” include the following substituents. More preferred substituent group a includes

1) a halogen atom

2) a hydroxyl group

3) a cyano group

4) a C₁₋₆ alkyl group

5) a C₁₋₆ alkoxy group

6) a C₁₋₆ alkylthio group

7) a C₁₋₆ alkylcarbonyl group

(wherein each substituent from 4) to 7) is optionally substituted with 1 to 5 of the same or different substituents selected from substituent group 3)

8) a 5- or 6-membered heteroaryloxy group

9) a 4- to 10-membered non-aryl heterocyclyl oxy group

10) a 5- or 6-membered heteroarylthio group

11) a 4- to 10-membered non-aryl heterocyclyl thio group

12) C₆₋₁₀ aryl

13) 5- or 6-membered heteroaryl

14) a 4- to 10-membered non-aryl heterocycle

(wherein each substituent from 4) to 14) is optionally substituted with 1 to 5 of substituent group β or 1) a C₁₋₆ alkyl group)

15) —NR^(10a)R^(11a)

16) —NR^(11b)—C(═O)R^(10b)

17) —NR^(12a)—C(═O)NR^(10c)R^(11c)

18) —C(═O)NR^(10d)R^(11d)

19) —C(═NR^(13a))R^(10e)

20) —C(═NR¹³)NR^(10f)R^(11e)

21) —NR^(11f)—C(═NR^(13c))R^(10g)

22) —NR^(12b)—C(═NR^(13d))—NR^(10h)R^(11g)

23) —C(═N—OR^(13a))R^(10e) and

24) —C(═N—OR^(13b))NR^(10f)R^(11e),

substituent group β is more preferably

1) a halogen atom,

2) a hydroxyl group,

3) a cyano group,

4) —NR^(15a)R^(16a),

5) —NR^(15b)—C(═O)R^(16b),

6) —NR^(17a)—C(═O)NR^(15c)R^(16c),

7) —C(═O)NR^(15d)R^(16d),

8) —C(═NR^(13e))R^(15e),

9) —C(═NR^(13f))NR^(15f)R^(16e),

10) —NR^(16f)—C(═NR^(13g))R^(15g),

11) —NR^(17b)—C(═NR^(13h))—NR^(15h)R^(16g)

12) —C(═N—OR^(13e))R^(15e), or

13) —C(═N—OR^(13f))NR^(15f)R^(16e),

R^(13a), R^(13b), R^(13c), R^(13d), R^(13e), R^(13f), R^(13g), and R^(13h) are the same or different, each independently a hydrogen atom, a hydroxyl group, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group,

R^(10a), R^(10b), R^(10c), R^(10d), R^(10e), R^(10f), R^(10g), R^(10h), R^(11a), R^(11b), R^(11c), R^(11d), R^(11e), R^(11f), R^(11g), R^(12a), R^(12b), R^(15a), R^(15b), R^(15c), R^(15d), R^(15e), R^(15f), R^(15g), R^(15h), R^(16a), R^(16b), R^(16c), R^(16d), R^(16e), R^(16f), R^(16g), R^(17a), and R^(17b) are the same or different, each independently a hydrogen atom or a C₁_alkyl group (wherein the group is optionally substituted with 1 to 3 of the same or different substituents selected from a hydroxyl group, a cyano group, a C₁₋₆ alkoxy group, and —NR^(18a)R^(18b)), and

R^(18a) and R^(18b) are the same or different, each independently a hydrogen atom or a C₁₋₆ alkyl group.

“C₁₋₆” means that the number of carbon atoms is 1 to 6. The same applies to other numbers. For example, “C₁₋₄” means that the number of carbon atoms is 1 to 4.

A “heteroatom” refers to an oxygen atom, a nitrogen atom, a sulfur atom, or the like.

A “halogen atom” refers to a fluorine atom, chlorine atom, bromine atom, or iodine atom, preferably a fluorine atom or chlorine atom, and still more preferably a fluorine atom. A “halogen atom” is also referred to as “halogen”.

“C₁₋₆ alkyl group” refers to a linear or branched saturated hydrocarbon group with 1 to 6 carbon atoms. “C₁₋₆ alkyl group” is preferably a “C₁₋₄ alkyl group”, more preferably a “C₁₋₃ alkyl group”, and still more preferably a “C₁₋₂ alkyl group”. Specific examples of “C₁₋₆ alkyl group” include, but are not limited to, methyl, ethyl, propyl, butyl, isopropyl, isobutyl, tert-butyl, sec-butyl, isopentyl, neopentyl, tert-pentyl, 1,2-dimethylpropyl, and the like.

“C₂₋₆ alkenyl group” refers to a linear or branched unsaturated hydrocarbon group with 2 to 6 carbon atoms, comprising one or more carbon-carbon double bonds. “C₂₋₆ alkenyl group” is preferably a “C₂₋₄ alkenyl group”. Specific examples of “C₂₋₆ alkenyl group” include, but are not limited to, a vinyl group, 1-propylenyl group, 2-propylenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-1-propylenyl group, 2-methyl-2-propylenyl group, and the like.

“C₂₋₆ alkynyl group” refers to a linear or branched unsaturated aliphatic hydrocarbon group comprising one or more carbon-carbon triple bonds. “C₂₋₆ alkynyl group” is preferably a “C₂₋₄ alkynyl group”. Specific examples thereof include, but are not limited to, an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 1-methyl-2-propynyl group, 3-butynyl group, 1-pentynyl group, 1-hexynyl group, and the like.

“C₃₋₂₀ alicyclic group” refers to a monocyclic or bicyclic non-aromatic hydrocarbon ring with 3 to 20 carbon atoms, including those with a partially unsaturated bond, those with a partially crosslinked structure, those that have a partially spiro form, and those having 1 or 2 carbonyl structures. “Alicyclic group” encompasses cycloalkyl groups, cycloalkenyl groups, and cycloalkynyl groups. “C₃₋₂₀ alicyclic group” is preferably a “C₃₋₁₀ alicyclic group”, and more preferably a “C₃₋₆ alicyclic group”. Specific examples of “C₃₋₂₀ alicyclic group” include, but are not limited to, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclohexadinyl group, cycloheptadinyl group, cyclooctadinyl group, adamantyl, norbornyl, and the like.

Specific examples of “C₃₋₂₀ alicyclic group” with a partially crosslinked structure include, but are not limited to, those with a structure shown below and the like.

“C₃₋₂₀ alicyclic group” also encompasses compounds fused to an aromatic ring. Specific examples thereof include the groups represented by the following and the like.

“C₃₋₁₀ alicyclic group” refers to the “C₃₋₂₀ alicyclic group” described above wherein the “C₃₋₁₀ alicyclic group” is a monovalent group.

“C₆₋₁₀ aryl” refers to a monocyclic or bicyclic aromatic hydrocarbon ring with 6 to 10 carbon atoms. Specific examples thereof include a phenyl group, 1-naphthyl group, 2-naphthyl group, and the like. Preferred C₆₋₁₀ aryl includes C₆ aryl and C₁₀ aryl.

“5- or 6-membered heteroaryl” refers to a monocyclic aromatic heterocycle consisting of 5 to 6 atoms, comprising 1 to 4 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.

“5- to 10-membered heteroaryl” refers to a monocyclic or bicyclic aromatic heterocycle consisting of 5 to 10 atoms, comprising 1 to 4 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.

“9- or 10-membered heteroaryl” refers to a bicyclic aromatic heterocycle consisting of 9 to 10 atoms, comprising 1 to 4 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom.

“5- or 6-membered nitrogen-containing heteroaryl” refers to a monocyclic aromatic heterocycle consisting of 5 to 6 atoms, comprising 0 to 3 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, in addition to 1 nitrogen atom.

Specific examples of “6-membered heteroaryl” include, but are not limited to, pyridine, pyridazine, pyrimidine, pyrazine, and the like.

Specific examples of “5-membered heteroaryl” include, but are not limited to, thiophene, pyrrole, thiazole, isothiazole, pyrazole, imidazole, furan, oxazole, isoxazole, oxadiazole, thiadiazole, triazole, tetrazole, and the like. 5-membered heteroaryl is preferably triazole, tetrazole, or thiadiazole, and more preferably thiadiazole.

Specific examples of “5- or 6-membered heteroaryl” include the specific examples for “5-membered heteroaryl” and “6-membered heteroaryl” described above.

“4- to 20-membered non-aryl heterocycle” refers to a monocyclic or bicyclic non-aromatic heterocycle comprised of 4 to 20 atoms, comprising 1 to 2 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, including those with a partially unsaturated bond, those with a partially crosslinked structure, and those that have a partially spiro form. A non-aryl heterocycle may form a fused ring with aryl or heteroaryl. When fused to, for example, C₆₋₁₀ aryl or 5- or 6-membered heteroaryl, such a heterocycle is still encompassed by a heterocycle. Such a heterocycle may comprise 1 or 2 carbonyl, thiocarbonyl, sulfinyl, or sulfonyl to make up the non-aryl heterocycle. For example, lactam, thiolactam, lactone, thiolactone, cyclic imide, cyclic carbamate, cyclic thiocarbamate, and other cyclic groups are also encompassed by said non-aryl heterocycle. In this regard, oxygen atoms of carbonyl, sulfinyl, and sulfonyl and sulfur atoms of thiocarbonyl are not included in the number of 4 to 20 members (size of ring) or the number of heteroatoms constituting the ring. Specific examples of “4- to 20-membered non-aryl heterocycle” include, but are not limited to, azetidine, pyrrolidine, piperidine, piperazine, morpholine, homopiperidine, oxetane, tetrahydrofuran, tetrahydropyran, and the like, those with a structure shown below, and the like.

Specific examples of “4- to 20-membered non-aryl heterocycle” with partial crosslinking or spiro structure include, but are not limited to, those with a structure shown below and the like.

“4- to 20-membered nitrogen-containing non-aryl heterocycle” refers to a monocyclic or bicyclic non-aromatic heterocycle comprised of 4 to 20 atoms, comprising 0 or 1 of the same or different heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom, in addition to 1 nitrogen atom, including those with a partially unsaturated bond, those with a partially crosslinked structure, and those that have a partially spiro form.

“4- to 10-membered non-aryl heterocycle” refers to the “4- to 20-membered non-aryl heterocycle” described above wherein “4- to 10-membered non-aryl heterocycle” is a monovalent group.

“4- to 10-membered nitrogen-containing non-aryl heterocycle” refers to the “4- to 20-membered nitrogen-containing non-aryl heterocycle” wherein the “4- to 10-membered nitrogen-containing non-aryl heterocycle” is a monovalent group.

“5- to 7-membered non-aryl heterocycle” refers to the “4- to 20-membered non-aryl heterocycle” described above wherein “5- to 7-membered non-aryl heterocycle” is a monovalent group.

“4- to 7-membered non-aryl heterocycle” refers to the “4- to 20-membered non-aryl heterocycle” described above wherein “4- to 7-membered non-aryl heterocycle” is a monovalent group.

Specific examples of “4-membered non-aryl heterocycle” include, but are not limited to, azetidine, oxetane, thietane, and the like.

Specific examples of “4-membered non-aryl heterocycle” with a partially unsaturated bond include, but are not limited to, those with a structure shown below and the like.

Specific examples of “5-membered non-aryl heterocycle” include, but are not limited to, pyrrolidine, pyrrolidone, oxazolidinone, tetrahydrofuran, tetrahydrothiophene, and the like.

Specific examples of “5-membered non-aryl heterocycle” with a partially unsaturated bond include, but are not limited to, those with a structure shown below and the like.

Specific examples of “5-membered non-aryl heterocycle” with a partially crosslinked structure include, but are not limited to, those with a structure shown below and the like.

Specific examples of “5-membered non-aryl heterocycle” comprising carbonyl, thiocarbonyl, or the like include, but are not limited to, those with a structure shown below and the like.

Specific examples of “6-membered non-aryl heterocycle” include, but are not limited to, piperidine, piperazine, morpholine, tetrahydropyran, tetrahydrothiopyran, and the like.

Specific examples of “6-membered non-aryl heterocycle” with a partially unsaturated bond include, but are not limited to, those with a structure shown below and the like.

Specific examples of “6-membered non-aryl heterocycle” with a partially crosslinked structure include, but are not limited to, those with a structure shown below and the like.

“C₁₋₆ alkoxy group” refers to a “C₁₋₆ alkyloxy group”, and the C₁₋₆ alkyl moiety is defined the same as the C₁₋₆ alkyl group described above. “C₁₋₆ alkoxy group” is preferably a “C₁₋₄ alkoxy group”, more preferably a “C₁₋₃ alkoxy group”, and still more preferably a “C₁₋₂ alkoxy group”. Specific examples of “C₁₋₆ alkoxy group” include, but are not limited to, a methoxy group, ethoxy group, propoxy group, butoxy group, isopropoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, isopentyloxy group, neopentyloxy group, tert-pentyloxy group, 1,2-dimethylpropoxy group, and the like.

“C₃₋₁₀ alicyclic oxy group” refers to a (C₃₋₁₀ alicyclic group)-O-group, and the C₃₋₁₀ alicyclic moiety is defined the same as a C₃₋₁₀ alicyclic group. “C₃₋₆ alicyclic oxy group” refers to a (C₃₋₆ alicyclic group)-O-group, and the C₃₋₆ alicyclic moiety is defined the same as a C₃₋₆ alicyclic group. “C₃₋₆ alicyclic oxy group” is preferably a “C₃₋₅ alicyclic oxy group”. Specific examples of “C₃₋₆ alicyclic oxy group” include, but are not limited to, a cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, and the like.

The C₆₋₁₀ aryl moiety of a “C₆₋₁₀ aryloxy group” is defined the same as the C₆₋₁₀ aryl described above. “C₆₋₁₀ aryloxy group” is preferably a “C₆ or C₁₀ aryloxy group”. Specific examples of “C₆₋₁₀ aryloxy group” include, but are not limited to, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, and the like.

The 5- or 6-membered heteroaryl moiety of “5- or 6-membered heteroaryloxy group” is defined the same as the “5-membered heteroaryl” or “6-membered heteroaryl” described above. Specific examples of “5- or 6-membered heteroaryloxy group” include, but are not limited to, a pyrazoyloxy group, triazoyloxy group, thiazoyloxy group, thiadiazoyloxy group, pyridyloxy group, pyridazoyloxy group, and the like.

The 4- to 10-membered non-aryl heterocycle moiety of “4- to 10-membered non-aryl heterocyclyl oxy group” is defined the same as the “4- to 10-membered non-aryl heterocycle” described above. “4- to 10-membered non-aryl heterocyclyl oxy group” is preferably a “4- to 6-membered non-aryl heterocyclyl oxy group”. Specific examples of “4- to 10-membered non-aryl heterocyclyl oxy group” include, but are not limited to, a tetrahydrofuranyloxy group, tetrahydropyranyloxy group, azetidinyloxy group, pyrrolidinyloxy group, piperidinyloxy group, and the like.

The C₁₋₆ alkyl moiety of “C₁₋₆ alkylthio group” is defined the same as the C₁₋₆ alkyl described above. “C₁₋₆ alkylthio group” is preferably a “C₁₋₄ alkylthio group”, and more preferably a “C₁₋₃ alkylthio group”. Specific examples of “C₁₋₆ alkylthio group” include, but are not limited to, a methylthio group, ethylthio group, propylthio group, butylthio group, isopropylthio group, isobutylthio group, tert-butylthio group, sec-butylthio group, isopentylthio group, neopentylthio group, tert-pentylthio group, 1,2-dimethylpropylthio group, and the like.

“C₃₋₁₀ alicyclic thio group” refers to a (C₃₋₁₃ alicyclic group)-S-group, and the C₃₋₁₀ alicyclic moiety is defined the same as the C₃₋₁₀ alicyclic group described above. “C₃₋₁₀ alicyclic thio group” is preferably a “C₃₋₆ alicyclic thio group”. Specific examples of “C₃₋₆ alicyclic thio group” include, but are not limited to, a cyclopropylthio group, cyclobutylthio group, cyclopentylthio group, cyclohexylthio group, and the like.

The C₆₋₁₀ aryl moiety of “C₆₋₁₀ arylthio group” is defined the same as the C₆₋₁₀ aryl described above. “C₆₋₁₀ arylthio group” is preferably a “C₆ or C₁₀ arylthio group”. Specific examples of “C₆₋₁₀ aryloxy group” include, but are not limited to, a phenylthio group, 1-naphthylthio group, 2-naphthylthio group, and the like.

The 5- or 6-membered heteroaryl moiety of “5- or 6-membered heteroarylthio group” is defined the same as the “5-membered heteroaryl” or “6-membered heteroaryl” described above. Specific examples of “5- or 6-membered heteroarylthio group” include, but are not limited to, a pyrazoylthio group, triazoylthio group, thiazoylthio group, thiadiazoylthio group, pyridylthio group, pyridazoylthio group, and the like.

The 4- to 10-membered non-aryl heterocycle moiety of “4- to 10-membered non-aryl heterocyclyl thio group” is defined the same as the “4- to 10-membered non-aryl heterocycle” described above. “4- to 10-membered non-aryl heterocyclyl thio group” is preferably a “4- to 6-membered non-aryl heterocyclyl thio group”. Specific examples of “4- to 10-membered non-aryl heterocyclyl thio group” include, but are not limited to, a tetrahydropyranylthio group, piperidinylthio group, and the like.

“C₁₋₆ alkylcarbonyl group” refers to a carbonyl group substituted with the “C₁₋₆ alkyl group” described above. “C₁₋₆ alkylcarbonyl group” is preferably a “C₁₋₄ alkylcarbonyl group”. Specific examples of “C₁₋₆ alkylcarbonyl group” include, but are not limited to, an acetyl group, propionyl group, butyryl group, and the like.

“C₃₋₁₀ alicyclic carbonyl group” refers to a carbonyl group substituted with the “C₃₋₁₀ alicyclic group” described above. “C₃₋₁₀ alicyclic carbonyl group” is preferably a “C₃₋₆ alicyclic carbonyl group”. Specific examples of “C₃₋₁₀ alicyclic carbonyl group” include, but are not limited to, a cyclopropylcarbonyl group, cyclopentylcarbonyl group, and the like.

“C₆₋₁₀ arylcarbonyl group” refers to a carbonyl group substituted with the “C₆₋₁₀ aryl” described above. “C₆₋₁₀ arylcarbonyl group” is preferably a “C₆ or C₁₀ arylcarbonyl group”. Specific examples of “C₆₋₁₀ arylcarbonyl group” include, but are not limited to, a benzoyl group, 1-naphthylcarbonyl group, 2-naphthylcarbonyl group, and the like.

“5- or 6-membered heteroarylcarbonyl group” refers to a carbonyl group substituted with the “5- or 6-membered heteroaryl” described above. Specific examples of “5- or 6-membered heteroarylcarbonyl group” include, but are not limited to, a pyrazoylcarbonyl group, triazoylcarbonyl group, thiazoylcarbonyl group, thiadiazoylcarbonyl group, pyridylcarbonyl group, pyridazoylcarbonyl group, and the like.

“4- to 10-membered non-aryl heterocyclyl carbonyl group” refers to a carbonyl group substituted with the “4- to 10-membered non-aryl heterocycle” described above. “4- to 10-membered non-aryl heterocyclyl carbonyl group” is preferably a “4- to 6-membered non-aryl heterocyclyl carbonyl group”. Specific examples of “4- to 10-membered non-aryl heterocyclyl carbonyl group” include, but are not limited to, an azetidinylcarbonyl group, pyrrolidinylcarbonyl group, piperidinylcarbonyl group, morpholinylcarbonyl group, and the like.

“C₁₋₆ alkylsulfonyl group” refers to a sulfonyl group substituted with the “C₁₋₆ alkyl group” described above. “C₁₋₆ alkylsulfonyl group” is preferably a “C₁₋₄ alkylsulfonyl group”. Specific examples of “C₁₋₆ alkylsulfonyl group” include, but are not limited to, a methylsulfonyl group, propionylsulfonyl group, butyrylsulfonyl group, and the like.

“C₃₋₁₀ alicyclic sulfonyl group” refers to a sulfonyl group substituted with the “C₃₋₁₀ alicyclic group” described above. “C₃₋₁₀ alicyclic sulfonyl group” is preferably a “C₃₋₆ alicyclic sulfonyl group”. Specific examples of “C₃₋₁₀ alicyclic sulfonyl group” include, but are not limited to, a cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, and the like.

“C₆₋₁₀ arylsulfonyl group” refers to a sulfonyl group substituted with the “C₆₋₁₀ aryl” described above. “C₆₋₁₀ arylsulfonyl group” is preferably a “C₆ or C₁₀ arylsulfonyl group”. Specific examples of “C₆₋₁₀ arylsulfonyl group” include, but are not limited to, a phenylsulfonyl group, 1-naphthylsulfonyl group, 2-naphthylsulfonyl group, and the like.

“5- or 6-membered heteroarylsulfonyl group” refers to a sulfonyl group substituted with the “5- or 6-membered heteroaryl” described above. Specific examples of “5- or 6-membered heteroarylsulfonyl group” include a pyrazoylsulfonyl group, triazoylsulfonyl group, thiazoylsulfonyl group, thiadiazoylsulfonyl group, pyridylsulfonyl group, pyridazoylsulfonyl group, and the like.

“C₁₋₆ alkylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from saturated hydrocarbon with 1 to 6 carbon atoms. “C₁₋₃ alkylene group” and “C₂₋₄ alkylene group” refer to substituents that are divalent groups due to removing two hydrogen atoms from saturated hydrocarbon with 1 to 3 carbon atoms and 2 to 4 carbon atoms, respectively.

“C₃₋₁₀ cycloalkylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from saturated cyclic hydrocarbon with 3 to 10 carbon atoms. “C₃₋₆ cycloalkylene group” and “C₄₋₆ cycloalkylene group” refer to substituents that are divalent groups due to removing two hydrogen atoms from saturated cyclic hydrocarbon with 3 to 6 carbon atoms and 4 to 6 carbon atoms, respectively.

“C₆₋₁₀ arylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from aromatic hydrocarbon with 6 to 10 carbon atoms. “C₆ arylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from aromatic hydrocarbon with 6 carbon atoms.

“5- or 6-membered heteroarylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from a 5- or 6-membered heteroaryl ring. “5-membered heteroarylene group” and “6-membered heteroarylene group” refer to substituents that are divalent groups due to removing two hydrogen atoms from 5-membered and 6-membered heteroaryl rings, respectively.

“4- to 10-membered non-aryl heterocyclylene group” refers to a substituent that is a divalent group due to removing two hydrogen atoms from a 4- to 10-membered non-aryl heterocycle. “4- to 5-membered non-aryl heterocyclylene group” and “4- to 6-membered non-aryl heterocyclylene group” refer to substituents that are divalent groups due to removing two hydrogen atoms from 4- to 5-membered and 4- to 6-membered non-aryl heterocycles, respectively.

A bond intersecting a wavy line in the description of a specific structure of R⁵ indicates a bond with L⁴. A bond intersecting a bond between ring atoms means that there are variables (e.g., R^(6a), R^(7a), and the like) at each of the substitutable positions on a monocycle or fused polycycle including the ring atoms. For example, for a monocyclic 5-membered ring (heteroaryl),

(wherein d is 3) is one of

and L⁴ attaches to a ring carbon atom of the 5-membered ring. For example, for a monocyclic 6-membered ring (heteroaryl),

(wherein d is 4) is one of

and L⁴ attaches to a ring carbon atom of the 6-membered ring. Alternatively, for example, for a monocyclic 5-membered ring (non-aryl heterocycle),

(wherein d is 7) is one of

and L⁴ attaches to a ring carbon atom of the 5-membered ring. For example, for a monocyclic 6-membered ring (non-aryl heterocycle),

(wherein d is 10) is one of

and L⁴ attaches to a ring carbon atom of the 6-membered ring.

Subscript d is the number of substitutable positions on a ring of R⁵, but is a number of substitutable positions excluding the attachment position to L⁴.

“Bioisostere” refers to another partial structure (functional group) serving the same biological role as a group (e.g., carboxyl group) in a drug molecule (prodrug structures are also encompassed as a concept of a bioisostere in the present invention). “Carboxylic acid isostere” refers to a bioisostere of carboxylic acid. Examples of the carboxylic acid isostere include, but are not limited to, —SO₃H, —SO₂NHR^(19a), —B(OR^(m1))₂, —PO(OR^(m1))(OR^(m2)) —CONHR^(19a), —CONHSO₂R^(19a), —CONR^(19a)CN, —CONHNHSO₂R^(19a), and substituents represented by the formulas (8A), (8B), (8C), (8D), (8E), (8F), (8G), (8H), (8I), (8J), (8K), (8L), (8M), (8N), (8O), (8P), (8Q), (8R), (8S), (8T), (8U), (8V), and (8W) described below (each of the substituents is further optionally substituted with 1 to 3 of the same or different R^(19b) at a chemical substitutable position),

wherein [in (8V) and (8W),

R^(s) is a hydrogen atom, a C₁₋₆ alkyl group, or a C₃₋₁₀ alicyclic group (wherein the C₁₋₆ alkyl group or C₃₋₁₀ alicyclic group is optionally substituted with 1 to 5 halogen atoms),

R^(t) is a hydrogen atom, a C₁₋₆ alkyl group, a C₁₋₆ alkoxy group, (wherein the C₁₋₆ alkyl group or C₁₋₆ alkoxy group is optionally substituted with 1 to 5 halogen atoms), a C₃₋₁₀ alicyclic group, a C₃₋₁₀ alicyclic oxy group, a phenyl group, a phenoxy group, a pyridyl group, or a pyridyloxy group, (wherein the C₃₋₁₀ alicyclic group, C₃₋₁₀ alicyclic oxy group, phenyl group, phenoxy group, pyridyl group, or pyridyloxy group is optionally substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a C₁₋₆ alkyl group, and a C₁₋₆ alkoxy group)],

R^(19a) and R^(19b) are the same or different, each independently representing a hydrogen atom, a hydroxyl group, a C₁₋₆ alkyl group, C₆₋₁₀ aryl, 5- or 6-membered heteroaryl, or a 4- to 10-membered non-aryl heterocycle,

R^(m1) represents

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle,

(wherein each substituent from 2) to 6) is optionally substituted),

wherein if R^(m1) is attached to a boron atom via an oxygen atom, two R^(m1), as C₂₋₄ alkylene, together with the boron atom and two oxygen atoms, may form a 5- to 7-membered non-aryl heterocycle (wherein an alkylene moiety is optionally substituted in the non-aryl heterocycle), and

R^(m2) represents a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group,

wherein, preferably,

R^(s) is a hydrogen atom or a C₁₋₆ alkyl group, and

R^(t) is a hydrogen atom, a C₁₋₆ alkyl group, a C₁₋₆ alkoxy group, a C₃₋₁₀ alicyclic group, or a C₃₋₁₀ alicyclic oxy group, or alternatively preferably,

R^(19a) and R^(19b) are the same or different, each independently a hydrogen atom, a hydroxyl group, or a C₁₋₆ alkyl group,

or also preferably

R^(m1) and R^(m2) are the same or different, each independently a hydrogen atom, a C₁₋₆ alkyl group, or a C₃₋₁₀ alicyclic group.

An exemplary embodiment of the compounds of the invention is a compound represented by formula (1a) or (1b):

or a pharmaceutically acceptable salt thereof, wherein

G is an oxygen atom, a sulfur atom, or —NR^(a1)—,

X is a hydroxyl group, an optionally substituted C₁₋₆ alkoxy group, or —NR^(a2)R^(b1),

R^(a1), R^(a2), and R^(b1) are the same or different, each independently

1) a hydrogen atom,

2) a C₁_alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl

5) 5- or 6-membered heteroaryl,

6) a 4- to 10-membered non-aryl heterocycle,

7) a C₁₋₆ alkylcarbonyl group,

8) a C₃₋₁₀ alicyclic carbonyl group,

9) a C₆₋₁₀ arylcarbonyl group,

10) a 5- or 6-membered heteroarylcarbonyl group,

11) a C₁₋₆ alkylsulfonyl group,

12) a C₃₋₁₀ alicyclic sulfonyl group,

13) a C₆₋₁₀ arylsulfonyl group,

14) a 5- or 6-membered heteroarylsulfonyl group, or

15) —OR^(c1),

(wherein each substituent from 2) to 14) is optionally substituted),

wherein R^(a2) and R^(b1) together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(c1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle,

(wherein each substituent from 2) to 6) is optionally substituted),

L¹ is a single bond, an oxygen atom, a sulfur atom, —SO—, —SO₂—, —NR^(d)—, —NR^(d)C(═O)—, or —NR^(d)SO₂—,

L² is a single bond or an optionally substituted C₁₋₆ alkylene group,

Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a carboxyl group,

5) a C₃₋₁₀ alicyclic group,

6) C₆₋₁₀ aryl,

7) 5- or 6-membered heteroaryl,

8) a 4- to 10-membered non-aryl heterocycle,

9) a C₁₋₆ alkoxy group,

10) a C₃₋₁₀ alicyclic oxy group,

11) a C₆₋₁₀ aryloxy group,

12) a 5- or 6-membered heteroaryloxy group,

13) a 4- to 10-membered non-aryl heterocyclyl oxy group,

14) a C₁₋₆ alkylthio group,

15) a C₃₋₁₀ alicyclic thio group,

16) a C₆₋₁₀ arylthio group,

17) a 5- or 6-membered heteroarylthio group,

18) a 4- to 10-membered non-aryl heterocyclyl thio group,

(wherein each substituent from 5) to 18) is optionally substituted),

19) —SO₂—NR^(e1)R^(f1),

20) —NR^(e1)—C(═O)OR^(f1),

21) —NR^(g1)—C(═O)NR^(e1)R^(f1),

22) —NR^(e1)—C(═S)R^(f1),

23) —NR^(e1)—C(═S)OR^(f1),

24) —NR^(g1)—C(═S)NR^(e1)R^(f1),

25) —NR^(g1)—CR^(e1)(═NR^(f1)),

26) —NR^(g1)—CR^(e1)(═N—OR^(f1)),

27) —NR^(h1)—C(═NR^(g1))NR^(e1)R^(f1),

28) —NR^(h1)—C(═N—OR^(g1))NR^(e1)R^(f1),

29) —NR^(i1)—C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

30) —NR^(i1)—C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

31) —NR^(e1)—SO₂—R^(f1),

32) —NR^(g1)—SO—NR^(e1)R^(f1),

33) —C(═O)OR^(e1),

34) —C(═S)OR^(e1),

35) —C(═S)NR^(e1)R^(f1),

36) —C(═S)NR^(e1)OR^(f1),

37) —C(═S)NR^(g1)—NR^(e1)R^(f1),

38) —C(═NR^(e1))R^(f1),

39) —C(═N—OR^(e1))R^(f1),

40) —C(═NR)NR^(g1)—NR^(e1)R^(f1),

41) —C(═N—OR)NR^(g1)—NR^(e1)R^(f1),

42) —NR^(e1)R^(f1),

43) —NR^(g1)—NR^(e1)R^(f1),

44) —NR^(e1)OR^(f1),

45) —NR^(e1)—C(═O)R^(f1),

46) —C(═O)NR^(e1)R^(f1),

47) —C(═O)NR^(e1)OR^(f1),

48) —C(═O)NR^(g1)—NR^(e1)R^(f1),

49) —C(═O)R^(e1),

50) —C(═NR^(h1))NR^(e1)R^(f1), or

51) —C(═N—OR^(h1))NR^(e1)R^(f1),

one of R¹, R², and R³ is formula (2):

wherein,

Y is an oxygen atom, a sulfur atom, or —NR^(j)—,

ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle,

L³ is —C(═O)—, —S(═O)—, or —S(═O)₂—,

L⁴ is

1) a single bond,

2) a C₁₋₆ alkylene group,

3) a C₃₋₁₀ cycloalkylene group,

4) a C₆₋₁₀ arylene group,

5) a 5- or 6-membered heteroarylene group,

6) a 4- to 10-membered non-aryl heterocyclylene group, or

7) —C(═N—OR^(h1))—,

(wherein each substituent from 2) to 6) is optionally substituted), and

R⁵ is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) a 4- to 10-membered non-aryl heterocycle,

5) C₆₋₁₀ aryl,

6) 5- or 6-membered heteroaryl,

7) a C₁₋₆ alkylthio group,

(wherein each substituent from 2) to 7) is optionally substituted), or

8) —NR^(e1)OH,

the remaining two (without the structure of formula (2) among R¹, R², and R³) are the same or different, each independently a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted C₁₋₆ alkylthio group, an optionally substituted 5- or 6-membered heteroaryl, or —NR^(a3)R^(b2),

R^(d), R^(e1), R^(e2), R^(f1), R^(f2), R^(g1), R^(g2), R^(h1), R^(h2), R^(i1), R^(i2), and R^(j) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₃₋₁₀ alicyclic group, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, or an optionally substituted 4- to 10-membered non-aryl heterocycle,

a combination of R^(e1) and R^(f1) or R^(e2) and R^(f2), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R⁴ is

1) —C(═O)R⁸,

2) —SO₂-L⁶-R⁸,

(wherein R⁸ in 1) and 2) is —NR^(a5)R^(b4), —NR^(a5)-L⁷-B(OR^(m1))₂, —OR^(m1), or an optionally substituted C₁₋₆ alkyl group, and L⁶ is a single bond or —NR^(a6)—),

3) —NR^(a4)R^(b3),

4) —B(OR^(m1))₂,

5) —PO(OR^(m1))(OR^(m2)),

6) optionally substituted 5-membered heteroaryl,

7) an optionally substituted 5-membered non-aryl heterocycle, or

8) a bioisostere of one of 1) to 7),

(wherein the formulas of 2), 4), 5), and 6) include a carboxylic acid isostere, and 8) may include them in duplicates),

R^(a3), R^(a4), R^(a5), R^(a6), R^(b2), R^(b3), and R^(b4) are the same or different, each independently having the same definition as R^(a1), R^(a2), and R^(b1), wherein a combination of R^(a3) and R^(b2), R^(a4) and R^(b3), or R^(a5) and R^(b4), when attached to the same nitrogen atom, together may form an optionally substituted 4- to 10-membered nitrogen-containing non-aryl heterocycle,

R^(m1) is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) C₆₋₁₀ aryl,

5) 5- or 6-membered heteroaryl, or

6) a 4- to 10-membered non-aryl heterocycle,

(wherein each substituent from 2) to 6) is optionally substituted),

wherein if R^(m1) is attached to a boron atom via an oxygen atom, two R^(m1), as C₂₋₄ alkylene, together with the boron atom and two oxygen atoms, may form a 5- to 7-membered non-aryl heterocycle (wherein an alkylene moiety is optionally substituted in the non-aryl heterocycle),

R^(m2) is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group, and

L⁷ is an optionally substituted C₁₋₃ alkylene group.

In some embodiments, Z-L²-L¹ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₁₋₆ alkylthio group. In one embodiment, L¹ is a single bond.

In some embodiments, L² is a single bond or an optionally substituted C₁₋₆ alkylene group. In one embodiment, L² is a single bond.

In some embodiments, Z is

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a carboxyl group,

5) a C₃₋₁₀ alicyclic group,

6) C₆₋₁₀ aryl,

7) 5- or 6-membered heteroaryl,

8) a 4- to 10-membered non-aryl heterocycle,

9) a C₁₋₆ alkoxy group,

10) a C₃₋₁₀ alicyclic oxy group,

11) a C₆₋₁₀ aryloxy group,

12) a 5- or 6-membered heteroaryloxy group,

13) a 4- to 10-membered non-aryl heterocyclyl oxy group,

14) a C₁₋₆ alkylthio group,

15) a C₃₋₁₀ alicyclic thio group,

16) a C₆₋₁₀ arylthio group,

17) a 5- or 6-membered heteroarylthio group,

18) a 4- to 10-membered non-aryl heterocyclyl thio group,

(wherein each substituent from 5) to 18) is optionally substituted),

19) —SO₂—NR^(e1)R^(f1),

20) —NR^(e1)—C(═O)OR^(f1),

21) —NR^(g1)—C(═O)NR^(e1)R^(f1),

22) —NR^(e1)—C(═S)R^(f1),

23) —NR^(e1)—C(═S)OR^(f1),

24) —NR^(g1)—C(═S)NR^(e1)R^(f1),

25) —NR^(g1)—CR^(e1)(═NR^(f1)),

26) —NR^(g1)—CR^(e1)(═N—OR^(f1)),

27) —NR^(h1)—C(═NR^(g1))NR^(e1)R^(f1),

28) —NR^(h1)—C(═N—OR^(g1))NR^(e1)R^(f1),

29) —NR^(i1)—C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

30) —NR^(i1)—C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

31) —NR^(e1)—SO₂—R^(f1),

32) —NR^(g1)—SO₂—NR^(e1)R^(f1),

33) —C(═O)OR^(e1),

34) —C(═S)OR^(e1),

35) —C(═S)NR^(e1)R^(f1),

36) —C(═S)NR^(e1)OR^(f1),

37) —C(═S)NR^(g1)—NR^(e1)R^(f1),

38) —C(═NR^(e1))R^(f1),

39) —C(═N—OR^(e1))R^(f1),

40) —C(═NR^(h1))NR^(g1)—NR^(e1)R^(f1),

41) —C(═N—OR^(h1))NR^(g1)—NR^(e1)R^(f1),

42) —NR^(e1)R^(f1),

43) —NR^(g1)—NR^(e1)R^(f1),

44) —NR^(e1)OR^(f1),

45) —NR^(e1)—C(═O)R^(f1),

46) —C(═O)NR^(e1)R^(f1),

47) —C(═O)NR^(e1)OR^(f1),

48) —C(═O)NR^(g1)—NR^(e1)R^(f1),

49) —C(═O)R^(e1),

50) —C(═NR^(g1))NR^(e1)R^(f1), or

51) —C(═N—OR^(h1))NR^(e1)R^(f1).

The R^(e1), R^(f1), R^(g1), and R^(h1) are the same as the definitions herein. In a preferred embodiment, Z is one of 1), 2), 5) to 8), 39), and 42). In one embodiment, Z is a hydrogen atom. Alternatively, in another embodiment, Z is an optionally substituted C₁₋₆ alkylthio group. In still another embodiment, Z is an optionally substituted C₁₋₆ alkyl group.

In a preferred embodiment, Z-L²-L¹ is a hydrogen atom. Alternatively, in another embodiment, Z-L²-L¹ is an optionally substituted C₁₋₆ alkylthio group. In still another embodiment, Z-L²-L¹ is an optionally substituted C₁₋₆ alkyl group.

In some embodiments, G is an oxygen atom, a sulfur atom, or —NR^(a1)—. In one embodiment, G is an oxygen atom or a sulfur atom. In a preferred embodiment, G is an oxygen atom. The R^(a1) is the same as the definition herein.

In some embodiments, X is a hydroxyl group, an optionally substituted C₁₋₆ alkoxy group, or —NR^(a2)R^(b1). In one embodiment, X is a hydroxyl group or an optionally substituted C₁₋₆ alkoxy group. In a preferred embodiment, X is a hydroxyl group. The R^(a2) and R^(b1) are the same as the definitions herein.

In some embodiments, one of R¹, R², and R³ is a group represented by formula (2):

wherein

Y is an oxygen atom, a sulfur atom, or —NR^(j)—,

ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle,

L³ is —C(═O)—, —S(═O)—, or —S(═O)₂—,

L⁴ is

1) a single bond,

2) a C₁₋₆ alkylene group,

3) a C₃₋₁₀ cycloalkylene group,

4) a C₆₋₁₀ arylene group

5) a 5- or 6-membered heteroarylene group,

6) a 4- to 10-membered non-aryl heterocyclylene group, or

7) —C(═N—OR^(h1))—,

(wherein each substituent from 2) to 6) is optionally substituted), and

R⁵ is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) a 4- to 10-membered non-aryl heterocycle,

5) C₆₋₁₉ aryl,

6) 5- or 6-membered heteroaryl,

7) a C₁₋₆ alkylthio group,

(wherein each substituent from 2) to 7) is optionally substituted), or

8) —NR^(e1)OH], and

the remaining two (without the structure of formula (2) among R¹, R², and R³) are the same or different, each independently a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted C₁₋₆ alkylthio group, optionally substituted 5- or 6-membered heteroaryl, or —NR^(a3)R^(b2), wherein R^(a3) and R^(b2) are the same as the definitions herein. In a preferred embodiment, R³ has the structure of formula (2).

In one embodiment, if R⁵ in formula (2) is 2) a C₁₋₆ alkyl group, 3) a C₃₋₁₀ alicyclic group, 4) a 4- to 10-membered non-aryl heterocycle, 5) C₆₋₁₀ aryl, 6) 5- or 6-membered heteroaryl, or 7) a C₁₋₆ alkylthio group, 2), 3), 4), 5), 6), and 7) are optionally substituted with a carboxyl group or a C₁₋₆ alkyl group substituted with a carboxyl group. In one embodiment, said 2), 3), 4), 5), 6), and 7) are optionally substituted with a carboxyl group. In one embodiment, said 2), 3), 4), 5), 6), and 7) are optionally substituted with a C₁₋₆ alkyl group substituted with a carboxyl group.

In one embodiment, if one of R¹, R², and R³ is represented by formula (2), the remaining two without the structure of formula (2) among R¹, R², and R³ are each independently selected from the group consisting of a hydrogen atom, a halogen atom, methyl, trifluoromethyl, methoxy, and trifluoromethoxy. In a preferred embodiment, R³ is represented by formula (2), and R¹ and R² are each independently selected from the group consisting of a hydrogen atom, a halogen atom, methyl, trifluoromethyl, methoxy, and trifluoromethoxy.

In some embodiments, Y is an oxygen atom, a sulfur atom, or —NR^(j)—. In one embodiment, Y is an oxygen atom or a sulfur atom. In a preferred embodiment, Y is an oxygen atom. The R^(j) is the same as the definition herein.

In some embodiments, ring A is an optionally substituted 4- to 20-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 10-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 7-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 7-membered nitrogen-containing non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 6-membered non-aryl heterocycle. In one embodiment, ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle. In one embodiment, ring A is an optionally substituted azetidine ring. In a specific embodiment of said embodiment, ring A is

wherein R⁶ represents a substituent on an azetidine ring and is defined the same as R^(6a), a bond that is orthogonal to a wavy line indicates a bond with Y, and a bond with * indicates a bond with L³. In a preferred embodiment, R⁶ are the same or different, each independently selected from the group consisting of 1) a hydrogen atom, 2) a halogen atom, 3) a C₁₋₆ alkyl group, and 4) a C₁₋₆ alkoxy group (wherein each of substituents 3) and 4) is optionally substituted with a halogen atom), and in a preferred embodiment, are selected from the group consisting of 1) a hydrogen atom, 2) a halogen atom, and 3) a C₁₋₆ alkyl group optionally substituted with a halogen atom, and most preferably are hydrogen atoms.

In a specific embodiment, ring A is

wherein m is 1, 2, or 3, n is 1, 2, or 3, m+n is 2, 3, 4, or 5, a bond that is orthogonal to a wavy line indicates a bond with Y, and a bond with * indicates a bond with L³. In one embodiment, m+n is 2, 3, or 4. In one embodiment, m+n is 2 or 3. In a preferred embodiment, m+n is 2. In a more preferred embodiment, m=1 and n=1.

In some embodiments, L³ is —C(═O)—, —S(═O)—, or —S(═O)₂—. In one embodiment, L³ is —C(═O)— or —S(═O)₂—. In a preferred embodiment, L³ is —C(═O)—.

In some embodiments, L⁴ is

1) a single bond,

2) a C₁₋₆ alkylene group,

3) a C₃₋₁₀ cycloalkylene group,

4) a C₆₋₁₀ arylene group

5) a 5- or 6-membered heteroarylene group,

6) a 4- to 10-membered non-aryl heterocyclylene group, or

7) —C(═N—OR^(h1))—,

(wherein each substituent from 2) to 6) is optionally substituted).

In one embodiment, L⁴ is a single bond, —C(═N—OR^(h1))— or an optionally substituted C₁₋₆ alkylene group, wherein R^(h1) is an optionally substituted C₁₋₆ alkyl group. In one embodiment, L⁴ is a single bond or a C₁₋₆ alkylene group optionally substituted with —NR¹R² or ═NOR²³, wherein R²¹, R²², and R²³ are each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted 4- to 10-membered non-aryl heterocyclyl carbonyl group. In a preferred embodiment, L⁴ is a bond, —CH₂—, —CH(NH₂)—, or —CH(NH₂)—CH₂—, wherein if an amino group is present in L⁴, carbon that attaches to the amino group attaches to L³.

In one embodiment, L⁴ is a single bond, —CH₂—, —CMe(NH₂)—, —CH(NHMe)-, —CD(NH₂)— (wherein D represents a heavy hydrogen atom), —CH(NH₂)—, or —CH₂CH₂—. In one embodiment, L⁴ is a single bond, —CH₂—, or —CH(NH₂)—.

In one embodiment, L⁴ is

1) —(CH₂)_(p)—CR¹⁰(NHR¹¹)—,

2) —(CH₂)_(q)—CR¹²R¹³—, or

3) —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CR¹²R¹³—, wherein p and q are independently 0 or 1, R¹⁰ is

1) a hydrogen atom,

2) a carboxyl group, or

3) —C(═O)NR^(10a)R^(10b),

R¹¹ is

1) a hydrogen atom,

2) —C(═O)R^(11a), or

3) an optionally substituted 5- or 6-membered non-aryl heterocyclyl carbonyl group,

wherein if R¹⁰ is —C(═O)NR^(10a)R^(10b), R^(10b) and R¹¹ together may form —CH₂CH₂—,

R¹² is

1) a hydrogen atom, or

2) an optionally substituted C₁₋₄ alkyl group,

R¹³ is

1) a hydrogen atom,

2) a hydroxyl group

3) an optionally substituted C₁₋₄ alkyl group

4) a sulfanyl group,

5) a carboxyl group,

6) an optionally substituted C₁₋₄ alkylthio group,

7) —NR^(13a)R^(13b),

8) —NR^(13a)—C(═O)R^(13b),

9) an optionally substituted 5- or 6-membered non-aryl heterocyclyl carbonylamino group,

10) —NR^(13a)—C(═O)NR^(13b)R^(13c),

11) —C(═O)NR^(13a)R^(13b),

12) —C(═O)NR^(13a)OR^(13b),

13) —S(═O)₂—R^(13a),

14) —S(═O)₂—NR^(13a)R^(13b),

15) —C(═O)NR^(13a)—S(═O)₂—R^(13b), or

16) —C(═O)NR^(13a)—S(═O)₂—NR^(13b)R^(13c), and

R^(10a), R^(10b), R^(11a), R^(13a), R^(13b), and R^(13c) are each independently a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

In one embodiment, L⁴ is —CH(NH₂) —CHR¹³—, wherein carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom, and

R¹³ is

1) —NH—C(═O)CH₃,

2) —NH—C(═O)NH₂,

3) —NH—C(═O)CH(NH₂)—CH₂C(═O)NH₂,

4) —NH—C(═O)CH₂—NH₂,

5) —NH—C(═O)CH(NH₂)—CH₂OH, or

6) a pyrrolidin-2-ylcarbonylamino group.

In one embodiment, L⁴ is —CH(NH₂)—CR²²R¹³—, wherein carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom or methyl,

R¹² is a hydrogen atom or methyl, and

R¹³ is a benzylthio group or a sulfanyl group.

In one embodiment, L⁴ is —CH(NH₂)—(CH₂)_(q)—CHR¹³—, wherein q is 0 or 1, and carbon that attaches to the NH₂ attaches to L³,

R⁵ is a hydrogen atom, and

R¹³ is

1) a carboxyl group,

2) —C(═O)NH₂,

3) —C(═O)NH(CH₃),

4) —C(═O)N(CH₃)₂,

5) —C(═O)NH—(CH₂)₂—OH,

6) —C(═O)NH—(CH₂)₂—NH₂,

7) —C(═O)NH—S(═O)₂—CH₃,

8) —C(═O)NHOH,

9) —S(═O)₂—NH₂,

10) —S(═O)₂—CH₃, or

11) a hydroxyl group.

In one embodiment, L⁴ is —CH(NHR¹¹)—CH₂—, wherein carbon that attaches to the NHR¹¹ attaches to L³,

R⁵ is hydrogen, and

R¹¹ is

1) —C(═O)CH(NH₂)—CH₂C(═O)NH₂,

2) —C(═O)CH₂—NH₂,

3) —C(═O)CH(CH₃)—NH₂,

4) —C(═O)CH(NH₂)—CH₂OH, or

5) pyrrolidin-2-ylcarbonyl.

In one embodiment, L⁴ is —CH(NHR¹¹)—CH(COOH)—, wherein carbon that attaches to the NHR¹¹ attaches to L³,

R⁵ is hydrogen, and

R¹¹ is

1) —C(═O)CH(NH₂)—CH₂C(═O)NH₂,

2) —C(═O)CH₂—NH₂,

3) —C(═O)CH(CH₃)—NH₂,

4) —C(═O)CH(NH₂)—CH₂OH, or

5) pyrrolidin-2-ylcarbonyl.

In one embodiment, L⁴ is —CHR¹³— or —CH₂—CHR¹³—,

R⁵ is hydrogen, and

R¹³ is —C(═O)NH₂ or —C(═O)NHOH.

In one embodiment, L¹ is —CH₂—CR¹⁰(NH₂)—, and the CH₂ group attaches to L³,

R⁵ is hydrogen, and

R¹⁰ is a carboxy group or —C(═O)NH₂.

In one embodiment, L⁴ is —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CHR¹³— or —CHR¹³—(CH₂)_(q)—CR¹⁰(NHR¹¹)—(CH₂)_(p)—, wherein q is 0 or 1,

R⁵ is hydrogen, (1) if L⁴ is —CHR¹³—(CH₂)_(q)—CR¹⁰(NHR¹¹) —(CH₂)_(p)—,

carbon of the —CHR¹³— group attaches to L³,

p is 0,

R¹⁰ is a hydrogen atom, a carboxyl group, or —C(═O)NHR^(10b),

R¹¹ is a hydrogen atom,

R^(10b) is a hydrogen atom,

wherein if R¹⁰ is —C(═O)NHR^(10b), R^(10b) and R¹¹ together may form —CH₂CH₂—, and

R¹³ is a hydrogen atom, and

(2) if L⁴ is —(CH₂)_(p)—CR¹⁰(NHR¹¹)—(CH₂)_(q)—CHR¹³—,

carbon of the —(CH₂)_(p)— group attaches to L³,

p is 1,

R¹⁰ and R¹¹ are both hydrogen atoms,

R¹³ is a carboxyl group or —C(═O)NR^(13a)R^(13b), and

R^(13a) and R^(13b) are each independently a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

In one embodiment, L⁴ is —CR¹²(NH₂)—,

R¹² is a hydrogen atom or a methyl group, and

R⁵ is a C₁₋₄ alkyl group optionally substituted with a hydroxyl group.

In some embodiments, R⁵ is

1) a hydrogen atom,

2) a C₁₋₆ alkyl group,

3) a C₃₋₁₀ alicyclic group,

4) a 4- to 10-membered non-aryl heterocycle,

5) C₆₋₁₀ aryl,

6) 5- or 6-membered heteroaryl,

7) a C₁₋₆ alkylthio group,

(wherein each substituent from 2) to 7) is optionally substituted), or

8) —NR^(e1)OH.

In one embodiment, R⁵ is a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted 4- to 10-membered non-aryl heterocycle, optionally substituted C₆₋₁₀ aryl, optionally substituted 5- or 6-membered heteroaryl, an optionally substituted C₁₋₆ alkylthio group, or —NR^(e1)OH, wherein R^(e1) is a hydrogen atom or an optionally substituted C₁₋₆ alkyl group. In one embodiment, R⁵ is an optionally substituted 5- or 6-membered heteroaryl or optionally substituted C₆₋₁₀ aryl.

In one embodiment, R⁵ is optionally substituted 5- or 6-membered heteroaryl. In one embodiment, R⁵ is an optionally substituted 4- to 10-membered non-aryl heterocycle. In one embodiment, R⁵ is a hydrogen atom or an optionally substituted C₁₋₄ alkyl group.

In one embodiment, R⁵ is selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) a nitro group,

5) halogen,

6) a C₁₋₄ alkyl group,

7) a C₃₋₁₀ alicyclic group,

8) a C₁₋₄ alkoxy group,

9) a C₃₋₁₀ alicyclic oxy group,

10) a C₆₋₁₀ aryloxy group,

11) a 5- or 6-membered heteroaryloxy group,

12) a 4- to 10-membered non-aryl heterocyclyl oxy group,

(wherein each substituent from 6) to 12) is optionally substituted),

13) —SO₂—NR^(e2)R^(f2),

14) —NR^(g2)—CR^(e2)(═NR^(f2)),

15) —NR^(g2)—CR^(e2)(═N—OR^(f2)),

16) —NR^(h2)—C(═NR^(g2))NR^(e2)R^(f2),

17) —NR^(h2)—C(═N—OR^(g2))NR^(e2)R^(f2),

18) —NR^(i2)—C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

19) —NR^(i2)—C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

20) —C(═NR^(e2))R^(f2),

21) —C(═N—OR^(e2))R^(f2),

22) —C(═NR^(h2))—NR^(e2)R^(f2),

23) —C(═NR^(g2)—NR^(e2)R^(f2),

24) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

25) —NR^(e2)R^(f2),

26) —NR^(g2)—NR^(e2)R^(f2)

27) —NR^(e2)OR^(f2),

28) —NR^(e2)—C(═O)R^(f2),

29) —C(═O)NR^(e2)R^(f2),

30) —C(═O)NR^(e2)OR^(f2),

31) —C(═O)NR^(g2)—NR^(e2)R^(f2),

32) —C(═O)R^(e2),

33) —C(═O)OR^(e2), and

34) —C(═N—OR^(h2))NR^(e2)R^(f2), and

each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted),

4) a C₃₋₁₀ alicyclic group

(wherein the alicyclic group is optionally substituted),

5) —C(═NR^(e2))R^(f2),

6) —C(═N—OR^(e2))R^(f2),

7) —SO₂—NR^(e2)R^(f2),

8) —C(═NR^(h2))—NR^(e2)R^(f2),

9) —C(═NR^(h2))NR^(g2)—NR^(e2)R^(f2),

10) —C(═N—OR^(h2))NR^(g2)—NR^(e2)R^(f2),

11) —C(═O)NR^(e2)R^(f2),

12) —C(═O)NR^(e2)OR^(f2),

13) —C(═O)NR^(g2)—NR^(e2)R^(f2),

14) —C(═O)R^(e2), and

15) —C(═N—OR^(h2))NR^(e2)R^(f2).

In one embodiment, R⁵ is 5- or 6-membered aryl or heteroaryl selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(6a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) halogen,

4) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), a 5- or 6-membered non-aryl heterocycle, —C(═O)OR^(f2), or a hydroxyl group),

5) a C₁₋₄ alkoxy group

6) —NR^(e2)R^(f2), and

7) —C(═O)OR^(e2), and

each R^(6b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group, and

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e2)R^(f2), —C(═O)NR^(e2)R^(f2), —C(═O)OR^(f2), or a hydroxyl group).

In one embodiment, R^(e2) and R^(f2) are the same or different, each independently a hydrogen atom, an optionally substituted C₁₋₆ alkyl group, or an optionally substituted C₃₋₁₀ alicyclic group. In one embodiment, R^(e2) and R^(f2) are the same or different, each independently a hydrogen atom or an optionally substituted C₁₋₆ alkyl group. In one embodiment, R^(e2) and R^(f2) are hydrogen atoms. In one embodiment, R^(6a) is —NR^(e2)R^(f2), and one of R^(e2) and R^(f2) is a hydrogen atom and the other is a C₁₋₄ alkyl group (wherein the alkyl group is optionally substituted with an amino group or a hydroxyl group).

In one embodiment, each R^(6a) may be independently halogen.

In one embodiment, each R^(6a) may be independently an alkylamino group substituted with an amino group. In one embodiment, each R^(6a) may be independently NR^(e2)R^(f2), wherein R^(e2) is a C₁₋₆ alkyl group, the C₁₋₆ alkyl group is substituted with —NR^(10a)R^(11a), and R^(10a) and R^(11a) are each independently defined the same as the description herein.

In one embodiment, each R^(6a) may be independently —C(═O) OH.

In one embodiment, each R^(6a) and/or each R^(6b) may be independently an alkyl group substituted with a carboxyl group. In one embodiment, each R^(6a) and/or each R^(6b) may be independently a C₁₋₄ alkyl group substituted with a —C(═C)OH group.

In one embodiment, R⁵ is a 4- to 6-membered non-aryl heterocycle selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(7a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a cyano group,

4) halogen,

5) a C₁₋₄ alkyl group,

6) a C₃₋₁₀ alicyclic group,

7) a C₁₋₄ alkoxy group,

8) a C₃₋₁₀ alicyclic oxy group,

9) a C₆₋₁₀ aryloxy group,

10) a 5- or 6-membered heteroaryloxy group,

11) a 4- to 10-membered non-aryl heterocyclyl oxy group,

(wherein each substituent from 5) to 11) is optionally substituted),

12) —SO₂—NR^(e3)R^(f3),

13) —NR^(g2)—CR^(e3)(═NR^(f3)),

14) —NR^(g2)—CR^(e3)(═N—OR^(f3)),

15) —NR^(h2)—C(═NR^(g2))NR^(e3)R^(f3),

16) —NR^(h2)—C(═N—OR^(g2))NR^(e3)R^(f3),

17) —NR^(i2)—C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

18) —NR^(i2)—C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

19) —C(═NR^(e3))R^(f3),

20) —C(═N—OR^(e3))R^(f3),

21) —C(═NR^(h2))—NR^(e3)R^(f3),

22) —C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

23) —C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

24) —NR^(e3)R^(f3),

25) —NR^(g2)—NR^(e3)R^(f3),

26) —NR^(e3)OR^(f3),

27) —NR^(e3)—C(═O)R^(f3),

28) —C(═O)NR^(e3)R^(f3),

29) —C(═O)NR^(e3)OR^(f3),

30) —C(═O)NR^(g2)—NR^(e3)R^(f3),

31) —C(═O)R^(e3),

32) —C(═O)OR^(e3), and

33) —C(═N—OR^(h2))NR^(e3)R^(f3),

each R^(7b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted),

4) a C₃₋₁₀ alicyclic group

(wherein the alicyclic group is optionally substituted),

5) —C(═NR^(e3))R^(f3),

6) —C(═N—OR^(e3))R^(f3),

7) —SO₂—NR^(e3)R^(f3),

8) —C(═NR^(h2))—NR^(e3)R^(f3),

9) —C(═NR^(h2))NR^(g2)—NR^(e3)R^(f3),

10) —C(═N—OR^(h2))NR^(g2)—NR^(e3)R^(f3),

11) —C(═O)NR^(e3)R^(f3),

12) —C(═O)NR^(e3)OR^(f3),

13) —C(═O)NR^(g2)—NR^(e3)R^(f3),

14) —C(═O)R^(e3), and

15) —C(═N—OR^(h2))NR^(e3)R^(f3), and

R^(e3) and R^(f3) are defined the same as R^(e2) and R^(f2) according to item B1.

In one embodiment, R⁵ is a 4- to 6-membered non-aryl heterocycle selected from the group consisting of

subscript d is the number of substitutable positions on a ring of R⁵,

each R^(7a) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group,

3) halogen,

4) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e3)R^(f3), a 5- or 6-membered non-aryl heterocycle, —C(═O)OR^(f3), or a hydroxyl group),

5) a C₁₋₄ alkoxy group

6) —NR^(e3)R^(f3),

7) —C(═O)OR^(e3),

8) C₆₋₁₀ aryl, and

9) —C(═O)NR^(e3)R^(f3),

each R^(7b) is independently selected from the group consisting of

1) a hydrogen atom,

2) a hydroxyl group, and

3) a C₁₋₄ alkyl group

(wherein the alkyl group is optionally substituted with NR^(e3)R^(f3), —C(═O)OR^(f3), or a hydroxyl group), and

R^(e3) and R^(f3) are defined the same as R^(e2) and R^(f2) according to any one of items B38 to B40.

In some embodiments, if one of R¹, R², and R³ is represented by formula (2), the remaining two are the same or different, each independently a hydrogen atom, a halogen atom, an optionally substituted C₁₋₆ alkyl group, an optionally substituted C₁₋₆ alkoxy group, an optionally substituted C₁₋₆ alkylthio group, optionally substituted 5- or 6-membered heteroaryl, or —NR^(a3)R^(b2), wherein R^(a3) and R^(b2) are the same as the descriptions herein. In a preferred embodiment, R³ is represented by formula (2).

In one embodiment where R³ is represented by formula (2), R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom,

3) a C₁₋₆ alkyl group,

4) a C₁₋₆ alkoxy group, and

5) a C₁₋₆ alkylthio group,

(wherein each substituent from 3) to 5) is optionally substituted).

In said embodiment, R¹ and R² are the same or different, each independently selected from the group consisting of

1) a hydrogen atom,

2) a halogen atom, and

3) an optionally substituted C₁₋₆ alkyl group.

In a preferred embodiment, R¹ and R² are both hydrogen atoms.

In some embodiments, R⁴ in formulas (1a) and (1b) is

1) —C(═O)R⁸,

2) —SO₂-L⁶-R⁸,

(wherein R⁸ in 1) and 2) is —NR^(a5)R^(b4), —NR^(a5)-L⁷-B(OR^(m1))₂, —OR^(m1), or an optionally substituted C₁₋₆ alkyl group, and L⁶ is a single bond or —NR^(a6)—),

3) —NR^(a4)R^(b3),

4) —B(OR^(m1))₂,

5) —PO(OR^(m1)) (OR^(m2)),

6) optionally substituted 5-membered heteroaryl,

7) an optionally substituted 5-membered non-aryl heterocycle, or

8) a bioisostere of one of 1) to 7),

(wherein the formulas of 2), 4), 5), and 6) include a carboxylic acid isostere, and 8) may include them in duplicates).

In one embodiment, R⁴ is —C(═O)—OR^(m1) or a carboxylic acid isostere thereof. In a preferred embodiment, R⁴ is 1) —COOH (i.e., a carboxyl group), or 2) a carboxylic acid isostere. The R^(a4), R^(a5), R^(a6), R^(b3), R^(b4), L⁷, R^(m1), and R^(m2) are the same as the definitions herein.

A specific example of a specific embodiment of the compound of the invention includes a compound represented by formula (3a) or (3b):

or a pharmaceutically acceptable salt thereof. X, R¹, R² and R³ in formula (3a) or (3b) are defined the same as the definitions herein, and R⁴ is selected from the group consisting of 1) —COOR^(m1) (wherein R^(m1) is a hydrogen atom, a C₁₋₆ alkyl group, a C₃₋₁₀ alicyclic group, C₆₋₁₀ aryl, 5- or 6-membered heteroaryl, or a 4- to 10-membered non-aryl heterocycle, wherein the C₁₋₆ alkyl group, the C₃₋₁₀ alicyclic group, the C₆₋₁₀ aryl, the 5- or 6-membered heteroaryl, and the 4- to 10-membered non-aryl heterocycle are each optionally substituted), and 2) a bioisostere of 1).

In a preferred embodiment, R⁴ is 1) —COOH (i.e., a carboxyl group) or 2) a carboxylic acid isostere.

A specific example of a preferred embodiment of the compound of the invention includes compounds represented by formulas (4a) and (4b)

or a pharmaceutically acceptable salt thereof. X, R⁴, Y, ring A, L³, L⁴, and R^(F) in formulas (4a) and (4b) are defined the same as the definitions herein, and R¹ and R² are the same or different, each independently a hydrogen atom, a halogen atom, a C₁₋₆ alkyl group, or a C₁₋₆ alkoxy group (wherein the C₁₋₆ alkyl group and C₁₋₆ alkoxy group are optionally substituted with 1 to 5 halogens).

A specific example of a still more preferred embodiment of the compound of the invention includes compounds represented by formulas (5a) and (5b):

or a pharmaceutically acceptable salt thereof. R¹, R², Y, L³, L⁴, R⁵, and ring A in formulas (5a) and (5b) are defined the same as the definitions herein, and ring A is an optionally substituted 4- to 6-membered nitrogen-containing non-aryl heterocycle.

A specific example of a yet still more preferred embodiment of the compound of the invention includes compounds represented by formulas (Ga) and (6b):

or a pharmaceutically acceptable salt thereof. L³, L⁴, and R⁵ in formulas (6a) and (6b) are defined the same as the definitions herein, m is an integer 1, 2, or 3, n is an integer 1, 2, or 3, and m+n is 2, 3, or 4. In one embodiment, m is 1 or 2, n is 1 or 2, and m+n is 2 or 3. In a preferred embodiment, m is 1, and n is 1.

A specific example of a preferred embodiment of the compound of the invention includes the following compound: a compound represented by

or a pharmaceutically acceptable salt thereof, wherein R^(ZL) is a substituent selected from the group consisting of the Z1 to Z4 described below, one of R¹, R², and R³ is

the remaining two are hydrogen atoms, linking group L^(a) is a substituent selected from the group consisting of L1 to L36 described below, and substituent Q^(a) is a substituent selected from the group consisting of Q1 to Q103 described below; R^(ZL):

linking group L^(a):

and substituent Q^(a):

A specific example of a more preferred embodiment of the compound of the invention includes a compound of the following formula:

a compound represented by

or a pharmaceutically acceptable salt thereof, wherein R^(ZL) is a substituent selected from the group consisting of Z1 to Z4 described above, R¹ and R² are hydrogen atoms, and R³ is

wherein linking group L^(a) is a substituent selected from the group consisting of L1 to L36 described above, and substituent Q^(a) is a substituent selected from the group consisting of Q1 to Q103 described above.

Examples of a more preferred embodiment of the compound of the invention include the compounds of the following Table (1) or a pharmaceutically acceptable salt thereof.

TABLE 1-1 Example R^(ZL) L^(a) Q^(a) 1 Z1 L1 Q1 2 Z1 L1 Q2 3 Z1 L1 Q3 4 Z1 L1 Q4 5 Z1 L1 Q5 6 Z1 L1 Q6 7 Z1 L1 Q7 8 Z1 L1 Q8 9 Z1 L1 Q9 10 Z1 L1 Q10 11 Z1 L1 Q11 12 Z1 L1 Q12 13 Z1 L1 Q13 14 Z1 L1 Q14 15 Z1 L1 Q15 16 Z1 L1 Q16 17 Z1 L1 Q17 18 Z1 L1 Q18 19 Z1 L1 Q19 20 Z1 L1 Q20 21 Z1 L1 Q21 22 Z1 L1 Q22 23 Z1 L1 Q23 24 Z1 L1 Q24 25 Z1 L1 Q25 26 Z1 L1 Q26 27 Z1 L1 Q27 28 Z1 L1 Q28 29 Z1 L1 Q29 30 Z1 L1 Q30 31 Z1 L1 Q31 32 Z1 L1 Q32 33 Z1 L1 Q33 34 Z1 L1 Q34 35 Z1 L1 Q35 30 Z1 L1 Q36 37 Z1 L1 Q37 38 Z1 L1 Q38 39 Z1 L1 Q39 40 Z1 L1 Q1 41 Z1 L2 Q2 42 Z1 L2 Q3 43 Z1 L2 Q4 44 Z1 L2 Q5 45 Z1 L2 Q6 46 Z1 L2 Q7 47 Z1 L2 Q8 48 Z1 L2 Q9 49 Z1 L2 Q10 50 Z1 L2 Q11 51 Z1 L2 Q12 52 Z1 L2 Q13 53 Z1 L2 Q14 54 Z1 L2 Q15 55 Z1 L2 Q16 56 Z1 L2 Q17 57 Z1 L2 Q18 58 Z1 L2 Q19 59 Z1 L2 Q20 60 Z1 L2 Q21 61 Z1 L2 Q22 62 Z1 L2 Q23 63 Z1 L2 Q24 64 Z1 L2 Q25 65 Z1 L2 Q26 66 Z1 L2 Q27 67 Z1 L2 Q28 68 Z1 L2 Q29 69 Z1 L2 Q30 70 Z1 L2 Q31 71 Z1 L2 Q32 72 Z1 L2 Q33 73 Z1 L2 Q34 74 Z1 L2 Q35 75 Z1 L2 Q36 76 Z1 L2 Q37 77 Z1 L2 Q38 78 Z1 L2 Q39 79 Z1 L3 Q1 80 Z1 L3 Q2

TABLE 1-2 81 Z1 L3 Q3 82 Z1 L3 Q4 83 Z1 L3 Q5 84 Z1 L3 Q6 85 Z1 L3 Q7 86 Z1 L3 Q8 87 Z1 L3 Q9 88 Z1 L3 Q10 89 Z1 L3 Q11 90 Z1 L3 Q12 91 Z1 L3 Q13 92 Z1 L3 Q14 93 Z1 L3 Q15 94 Z1 L3 Q16 95 Z1 L3 Q17 96 Z1 L3 Q18 97 Z1 L3 Q19 98 Z1 L3 Q20 99 Z1 L3 Q21 100 Z1 L3 Q22 101 Z1 L3 Q23 102 Z1 L3 Q24 103 Z1 L3 Q25 104 Z1 L3 Q26 105 Z1 L3 Q27 106 Z1 L3 Q28 107 Z1 L3 Q29 108 Z1 L3 Q30 109 Z1 L3 Q31 110 Z1 L3 Q32 111 Z1 L3 Q33 112 Z1 L3 Q34 113 Z1 L3 Q35 114 Z1 L3 Q36 115 Z1 L3 Q37 116 Z1 L3 Q38 117 Z1 L3 Q39 118 Z1 L4 Q1 119 Z1 L4 Q2 120 Z1 L4 Q3 121 Z1 L4 Q4 122 Z1 L4 Q5 123 Z1 L4 Q6 124 Z1 L4 Q7 125 Z1 L4 Q8 126 Z1 L4 Q9 127 Z1 L4 Q10 128 Z1 L4 Q11 129 Z1 L4 Q12 130 Z1 L4 Q13 131 Z1 L4 Q14 132 Z1 L4 Q15 133 Z1 L4 Q16 134 Z1 L4 Q17 135 Z1 L4 Q18 130 Z1 L4 Q19 137 Z1 L4 Q20 138 Z1 L4 Q21 139 Z1 L4 Q22 140 Z1 L4 Q23 141 Z1 L4 Q24 142 Z1 L4 Q25 143 Z1 L4 Q26 144 Z1 L4 Q27 145 Z1 L4 Q28 146 Z1 L4 Q29 147 Z1 L4 Q30 148 Z1 L4 Q31 149 Z1 L4 Q32 150 Z1 L4 Q33 151 Z1 L4 Q34 152 Z1 L4 Q35 153 Z1 L4 Q36 154 Z1 L4 Q37 155 Z1 L4 Q38 156 Z1 L4 Q39 157 Z1 L5 Q1 158 Z1 L5 Q2 159 Z1 L5 Q3 160 Z1 L5 Q4 161 Z1 L5 Q5 162 Z1 L5 Q6 163 Z1 L5 Q7 164 Z1 L5 Q8 165 Z1 L5 Q9 166 Z1 L5 Q10 167 Z1 L5 Q11 168 Z1 L5 Q12 169 Z1 L5 Q13 170 Z1 L5 Q14 171 Z1 L5 Q15 172 Z1 L5 Q16 173 Z1 L5 Q17 174 Z1 L5 Q18 175 Z1 L5 Q19 176 Z1 L5 Q20 177 Z1 L5 Q21 178 Z1 L5 Q22 179 Z1 L5 Q23 180 Z1 L5 Q24 181 Z1 L5 Q25 182 Z1 L5 Q26 183 Z1 L5 Q27 184 Z1 L5 Q28 185 Z1 L5 Q29 186 Z1 L5 Q30 187 Z1 L5 Q31 188 Z1 L5 Q32 189 Z1 L5 Q33 190 Z1 L5 Q34 191 Z1 L5 Q35 192 Z1 L5 Q36 193 Z1 L5 Q37 194 Z1 L5 Q38 195 Z1 L5 Q39 196 Z1 L6 Q1 197 Z1 L6 Q2 198 Z1 L6 Q3 199 Z1 L6 Q4 200 Z1 L6 Q5 201 Z1 L6 Q6 202 Z1 L6 Q7 203 Z1 L6 Q8 204 Z1 L6 Q9 205 Z1 L6 Q10 206 Z1 L6 Q11 207 Z1 L6 Q12 208 Z1 L6 Q13 209 Z1 L6 Q14 210 Z1 L6 Q15 211 Z1 L6 Q16 212 Z1 L6 Q17 213 Z1 L6 Q18 214 Z1 L6 Q19 215 Z1 L6 Q20 216 Z1 L6 Q21

TABLE 1-3 222 Z1 L6 Q27 223 Z1 L6 Q28 224 Z1 L6 Q29 225 Z1 L6 Q30 226 Z1 L6 Q31 227 Z1 L6 Q32 228 Z1 L6 Q33 229 Z1 L6 Q34 230 Z1 L6 Q35 231 Z1 L6 Q36 232 Z1 L6 Q37 233 Z1 L6 Q38 234 Z1 L6 Q39 235 Z1 L7 Q1 236 Z1 L7 Q2 237 Z1 L7 Q3 238 Z1 L7 Q4 239 Z1 L7 Q5 240 Z1 L7 Q6 241 Z1 L7 Q7 242 Z1 L7 Q8 243 Z1 L7 Q9 244 Z1 L7 Q10 245 Z1 L7 Q11 246 Z1 L7 Q12 247 Z1 L7 Q13 248 Z1 L7 Q14 249 Z1 L7 Q15 250 Z1 L7 Q16 251 Z1 L7 Q17 252 Z1 L7 Q18 253 Z1 L7 Q19 254 Z1 L7 Q20 255 Z1 L7 Q21 256 Z1 L7 Q22 257 Z1 L7 Q23 258 Z1 L7 Q24 259 Z1 L7 Q25 260 Z1 L7 Q26 261 Z1 L7 Q27 262 Z1 L7 Q28 263 Z1 L7 Q29 264 Z1 L7 Q30 265 Z1 L7 Q31 266 Z1 L7 Q32 267 Z1 L7 Q33 268 Z1 L7 Q34 269 Z1 L7 Q35 270 Z1 L7 Q36 271 Z1 L7 Q37 272 Z1 L7 Q38 273 Z1 L7 Q39 274 Z1 L8 Q1 275 Z1 L8 Q2 276 Z1 L8 Q3 277 Z1 L8 Q4 278 Z1 L8 Q5 279 Z1 L8 Q6 280 Z1 L8 Q7 281 Z1 L8 Q8 282 Z1 L8 Q9 283 Z1 L8 Q10 284 Z1 L8 Q11 285 Z1 L8 Q12 286 Z1 L8 Q13 287 Z1 L8 Q14 288 Z1 L8 Q15 289 Z1 L8 Q16 290 Z1 L8 Q17 291 Z1 L8 Q18 292 Z1 L8 Q19 293 Z1 L8 Q20 294 Z1 L8 Q21 295 Z1 L8 Q22 296 Z1 L8 Q23 297 Z1 L8 Q24 298 Z1 L8 Q25 299 Z1 L8 Q26 300 Z1 L8 Q27 301 Z1 L8 Q28 302 Z1 L8 Q29 303 Z1 L8 Q30 304 Z1 L8 Q31 305 Z1 L8 Q32 306 Z1 L8 Q33 307 Z1 L8 Q34 308 Z1 L8 Q35 309 Z1 L8 Q36 310 Z1 L8 Q37 311 Z1 L8 Q38 312 Z1 L8 Q39 313 Z1 L9 Q1 314 Z1 L9 Q2 315 Z1 L9 Q3 316 Z1 L9 Q4 317 Z1 L9 Q5 318 Z1 L9 Q6 319 Z1 L9 Q7 320 Z1 L9 Q8 321 Z1 L9 Q9 322 Z1 L9 Q10 323 Z1 L9 Q11 324 Z1 L9 Q12 325 Z1 L9 Q13 326 Z1 L9 Q14 327 Z1 L9 Q15 328 Z1 L9 Q16 329 Z1 L9 Q17 330 Z1 L9 Q18 331 Z1 L9 Q19 332 Z1 L9 Q20 333 Z1 L9 Q21 334 Z1 L9 Q22 335 Z1 L9 Q23 336 Z1 L9 Q24 337 Z1 L9 Q25 338 Z1 L9 Q26 339 Z1 L9 Q27 340 Z1 L9 Q28 341 Z1 L9 Q29 342 Z1 L9 Q30 343 Z1 L9 Q31 344 Z1 L9 Q32 345 Z1 L9 Q33 346 Z1 L9 Q34 347 Z1 L9 Q35 348 Z1 L9 Q36 349 Z1 L9 Q37 350 Z1 L9 Q38 351 Z1 L9 Q39 352 Z1 L10 Q1 353 Z1 L10 Q2 354 Z1 L10 Q3 355 Z1 L10 Q4 356 Z1 L10 Q5 357 Z1 L10 Q6 358 Z1 L10 Q7 359 Z1 L10 Q8 360 Z1 L10 Q9 361 Z1 L10 Q10 362 Z1 L10 Q11

TABLE 1-4 363 Z1 L10 Q12 364 Z1 L10 Q13 365 Z1 L10 Q14 366 Z1 L10 Q15 367 Z1 L10 Q16 368 Z1 L10 Q17 369 Z1 L10 Q18 370 Z1 L10 Q19 371 Z1 L10 Q20 372 Z1 L10 Q21 373 Z1 L10 Q22 374 Z1 L10 Q23 375 Z1 L10 Q24 376 Z1 L10 Q25 377 Z1 L10 Q26 378 Z1 L10 Q27 379 Z1 L10 Q28 380 Z1 L10 Q29 381 Z1 L10 Q30 382 Z1 L10 Q31 383 Z1 L10 Q32 384 Z1 L10 Q33 385 Z1 L10 Q34 386 Z1 L10 Q35 387 Z1 L10 Q36 388 Z1 L10 Q37 389 Z1 L10 Q38 390 Z1 L10 Q39 391 Z1 L11 Q1 392 Z1 L11 Q2 393 Z1 L11 Q3 394 Z1 L11 Q4 395 Z1 L11 Q5 396 Z1 L11 Q6 397 Z1 L11 Q7 398 Z1 L11 Q8 399 Z1 L11 Q9 400 Z1 L11 Q10 401 Z1 L11 Q11 402 Z1 L11 Q12 403 Z1 L11 Q13 404 Z1 L11 Q14 405 Z1 L11 Q15 406 Z1 L11 Q16 407 Z1 L11 Q17 408 Z1 L11 Q18 409 Z1 L11 Q19 410 Z1 L11 Q20 411 Z1 L11 Q21 412 Z1 L11 Q22 413 Z1 L11 Q23 414 Z1 L11 Q24 415 Z1 L11 Q25 416 Z1 L11 Q26 417 Z1 L11 Q27 418 Z1 L11 Q28 419 Z1 L11 Q29 420 Z1 L11 Q30 421 Z1 L11 Q31 422 Z1 L11 Q32 423 Z1 L11 Q33 424 Z1 L11 Q34 425 Z1 L11 Q35 426 Z1 L11 Q36 427 Z1 L11 Q37 428 Z1 L11 Q38 429 Z1 L11 Q39 430 Z1 L12 Q1 431 Z1 L12 Q2 432 Z1 L12 Q3 433 Z1 L12 Q4 434 Z1 L12 Q5 435 Z1 L12 Q6 436 Z1 L12 Q7 437 Z1 L12 Q8 433 Z1 L12 Q9 439 Z1 L12 Q10 440 Z1 L12 Q11 441 Z1 L12 Q12 442 Z1 L12 Q13 443 Z1 L12 Q14 444 Z1 L12 Q15 445 Z1 L12 Q16 446 Z1 L12 Q17 447 Z1 L12 Q18 448 Z1 L12 Q19 449 Z1 L12 Q20 450 Z1 L12 Q21 451 Z1 L12 Q22 452 Z1 L12 Q23 453 Z1 L12 Q24 454 Z1 L12 Q25 455 Z1 L12 Q26 456 Z1 L12 Q27 457 Z1 L12 Q28 458 Z1 L12 Q29 459 Z1 L12 Q30 460 Z1 L12 Q31 461 Z1 L12 Q32 462 Z1 L12 Q33 463 Z1 L12 Q34 464 Z1 L12 Q35 465 Z1 L12 Q36 466 Z1 L12 Q37 467 Z1 L12 Q38 468 Z1 L12 Q39 469 Z1 L13 Q1 470 Z1 L13 Q2 471 Z1 L13 Q3 472 Z1 L13 Q4 473 Z1 L13 Q5 474 Z1 L13 Q6 475 Z1 L13 Q7 476 Z1 L13 Q8 477 Z1 L13 Q9 478 Z1 L13 Q10 479 Z1 L13 Q11 480 Z1 L13 Q12 481 Z1 L13 Q13 482 Z1 L13 Q14 483 Z1 L13 Q15 484 Z1 L13 Q16 485 Z1 L13 Q17 488 Z1 L13 Q18 487 Z1 L13 Q19 488 Z1 L13 Q20 489 Z1 L13 Q21 490 Z1 L13 Q22 491 Z1 L13 Q23 492 Z1 L13 Q24 493 Z1 L13 Q25 494 Z1 L13 Q26 495 Z1 L13 Q27 496 Z1 L13 Q28 497 Z1 L13 Q29 498 Z1 L13 Q30 499 Z1 L13 Q31 500 Z1 L13 Q32 501 Z1 L13 Q33 502 Z1 L13 Q34 503 Z1 L13 Q35

TABLE 1-5 504 Z1 L13 Q36 505 Z1 L13 Q37 506 Z1 L13 Q38 507 Z1 L13 Q39 508 Z1 L14 Q1 509 Z1 L14 Q2 510 Z1 L14 Q3 511 Z1 L14 Q4 512 Z1 L14 Q5 513 Z1 L14 Q6 514 Z1 L14 Q7 515 Z1 L14 Q8 516 Z1 L14 Q9 517 Z1 L14 Q10 518 Z1 L14 Q11 519 Z1 L14 Q12 520 Z1 L14 Q13 521 Z1 L14 Q14 522 Z1 L14 Q15 523 Z1 L14 Q16 524 Z1 L14 Q17 525 Z1 L14 Q18 526 Z1 L14 Q19 5271 Z1 L14 Q20 528 Z1 L14 Q21 529 Z1 L14 Q22 530 Z1 L14 Q23 531 Z1 L14 Q24 532 Z1 L14 Q25 533 Z1 L14 Q26 534 Z1 L14 Q27 535 Z1 L14 Q28 536 Z1 L14 Q29 537 Z1 L14 Q30 533 Z1 L14 Q31 539 Z1 L14 Q32 540 Z1 L14 Q33 541 Z1 L14 Q34 542 Z1 L14 Q35 543 Z1 L14 Q36 544 Z1 L14 Q37 545 Z1 L14 Q38 546 Z1 L14 Q39 547 Z2 L1 Q1 548 Z2 L1 Q2 549 Z2 L1 Q3 550 Z2 L1 Q4 551 Z2 L1 Q5 552 Z2 L1 Q6 553 Z2 L1 Q7 554 Z2 L1 Q8 555 Z2 L1 Q9 556 Z2 L1 Q10 557 Z2 L1 Q11 558 Z2 L1 Q12 559 Z2 L1 Q13 560 Z2 L1 Q14 561 Z2 L1 Q15 562 Z2 L1 Q16 563 Z2 L1 Q17 564 Z2 L1 Q18 565 Z2 L1 Q19 566 Z2 L1 Q20 567 Z2 L1 Q21 568 Z2 L1 Q22 569 Z2 L1 Q23 570 Z2 L1 Q24 571 Z2 L1 Q25 572 Z2 L1 Q26 573 Z2 L1 Q27 574 Z2 L1 Q28 575 Z2 L1 Q29 576 Z2 L1 Q30 577 Z2 L1 Q31 578 Z2 L1 Q32 579 Z2 L1 Q33 580 Z2 L1 Q34 581 Z2 L1 Q35 582 Z2 L1 Q36 583 Z2 L1 Q37 584 Z2 L1 Q38 585 Z2 L1 Q39 586 Z2 L2 Q1 587 Z2 L2 Q2 588 Z2 L2 Q3 589 Z2 L2 Q4 590 Z2 L2 Q5 591 Z2 L2 Q6 592 Z2 L2 Q7 593 Z2 L2 Q3 594 Z2 L2 Q9 595 Z2 L2 Q10 596 Z2 L2 Q11 597 Z2 L2 Q12 598 Z2 L2 Q13 599 Z2 L2 Q14 600 Z2 L2 Q15 601 Z2 L2 Q16 602 Z2 L2 Q17 603 Z2 L2 Q18 604 Z2 L2 Q19 605 Z2 L2 Q20 606 Z2 L2 Q21 607 Z2 L2 Q22 608 Z2 L2 Q23 609 Z2 L2 Q24 610 Z2 L2 Q25 611 Z2 L2 Q26 612 Z2 L2 Q27 613 Z2 L2 Q28 614 Z2 L2 Q29 615 Z2 L2 Q30 616 Z2 L2 Q31 617 Z2 L2 Q32 618 Z2 L2 Q33 619 Z2 L2 Q34 620 Z2 L2 Q35 621 Z2 L2 Q36 622 Z2 L2 Q37 623 Z2 L2 Q38 624 Z2 L2 Q39 625 Z2 L3 Q1 626 Z2 L3 Q2 627 Z2 L3 Q3 628 Z2 L3 Q4 629 Z2 L3 Q5 630 Z2 L3 Q6 631 Z2 L3 Q7 632 Z2 L3 Q8 633 Z2 L3 Q9 634 Z2 L3 Q10 635 Z2 L3 Q11 636 Z2 L3 Q12 637 Z2 L3 Q13 638 Z2 L3 Q14 639 Z2 L3 Q15 640 Z2 L3 Q16 641 Z2 L3 Q17 642 Z2 L3 Q18 643 Z2 L3 Q19 644 Z2 L3 Q20

TABLE 1-6 645 Z2 L3 Q21 646 Z2 L3 Q22 647 Z2 L3 Q23 648 Z2 L3 Q24 649 Z2 L3 Q25 650 Z2 L3 Q26 651 Z2 L3 Q27 652 Z2 L3 Q28 653 Z2 L3 Q29 654 Z2 L3 Q30 655 Z2 L3 Q31 656 Z2 L3 Q32 657 Z2 L3 Q33 658 Z2 L3 Q34 659 Z2 L3 Q35 660 Z2 L3 Q36 661 Z2 L3 Q37 662 Z2 L3 Q38 663 Z2 L3 Q39 664 Z2 L4 Q1 665 Z2 L4 Q2 666 Z2 L4 Q3 667 Z2 L4 Q4 668 Z2 L4 Q5 669 Z2 L4 Q6 670 Z2 L4 Q7 671 Z2 L4 Q8 672 Z2 L4 Q9 673 Z2 L4 Q10 674 Z2 L4 Q11 675 Z2 L4 Q12 676 Z2 L4 Q13 677 Z2 L4 Q14 678 Z2 L4 Q15 679 Z2 L4 Q16 680 Z2 L4 Q17 681 Z2 L4 Q18 682 Z2 L4 Q19 683 Z2 L4 Q20 684 Z2 L4 Q21 685 Z2 L4 Q22 686 Z2 L4 Q23 687 Z2 L4 Q24 688 Z2 L4 Q25 689 Z2 L4 Q26 690 Z2 L4 Q27 691 Z2 L4 Q23 692 Z2 L4 Q29 693 Z2 L4 Q30 694 Z2 L4 Q31 695 Z2 L4 Q32 696 Z2 L4 Q33 697 Z2 L4 Q34 698 Z2 L4 Q35 699 Z2 L4 Q36 700 Z2 L4 Q37 701 Z2 L4 Q38 702 Z2 L4 Q39 703 Z2 L5 Q1 704 Z2 L5 Q2 705 Z2 L5 Q3 706 Z2 L5 Q4 707 Z2 L5 Q5 708 Z2 L5 Q6 709 Z2 L5 Q7 710 Z2 L5 Q8 711 Z2 L5 Q9 712 Z2 L5 Q10 713 Z2 L5 Q11 714 Z2 L5 Q12 715 Z2 L5 Q13 716 Z2 L5 Q14 717 Z2 L5 Q15 718 Z2 L5 Q16 719 Z2 L5 Q17 720 Z2 L5 Q18 721 Z2 L5 Q19 722 Z2 L5 Q20 723 Z2 L5 Q21 724 Z2 L5 Q22 725 Z2 L5 Q23 726 Z2 L5 Q24 727 Z2 L5 Q25 728 Z2 L5 Q26 729 Z2 L5 Q27 730 Z2 L5 Q28 731 Z2 L5 Q29 732 Z2 L5 Q30 733 Z2 L5 Q31 734 Z2 L5 Q32 735 Z2 L5 Q33 736 Z2 L5 Q34 737 Z2 L5 Q35 738 Z2 L5 Q36 739 Z2 L5 Q37 740 Z2 L5 Q38 741 Z2 L5 Q39 742 Z2 L6 Q1 743 Z2 L6 Q2 744 Z2 L6 Q3 745 Z2 L6 Q4 746 Z2 L6 Q5 747 Z2 L6 Q6 748 Z2 L6 Q7 749 Z2 L6 Q8 750 Z2 L6 Q9 751 Z2 L6 Q10 752 Z2 L6 Q11 753 Z2 L6 Q12 754 Z2 L6 Q13 755 Z2 L6 Q14 756 Z2 L6 Q15 757 Z2 L6 Q16 758 Z2 L6 Q17 759 Z2 L6 Q18 760 Z2 L6 Q19 761 Z2 L6 Q20 762 Z2 L6 Q21 763 Z2 L6 Q22 764 Z2 L6 Q23 765 Z2 L6 Q24 766 Z2 L6 Q25 767 Z2 L6 Q26 768 Z2 L6 Q27 769 Z2 L6 Q28 770 Z2 L6 Q29 771 Z2 L6 Q30 772 Z2 L6 Q31 773 Z2 L6 Q32 774 Z2 L6 Q33 775 Z2 L6 Q34 776 Z2 L6 Q35 777 Z2 L6 Q36 778 Z2 L6 Q37 779 Z2 L6 Q38 780 Z2 L6 Q39 781 Z2 L7 Q1 782 Z2 L7 Q2 783 Z2 L7 Q3 784 Z2 L7 Q4 785 Z2 L7 Q5

TABLE 1-7 786 Z2 L7 Q6 787 Z2 L7 Q7 788 Z2 L7 Q8 789 Z2 L7 Q9 790 Z2 L7 Q10 791 Z2 L7 Q11 792 Z2 L7 Q12 793 Z2 L7 Q13 794 Z2 L7 Q14 795 Z2 L7 Q15 796 Z2 L7 Q16 797 Z2 L7 Q17 798 Z2 L7 Q18 799 Z2 L7 Q19 800 Z2 L7 Q20 801 Z2 L7 Q21 802 Z2 L7 Q22 803 Z2 L7 Q23 804 Z2 L7 Q24 805 Z2 L7 Q25 806 Z2 L7 Q26 807 Z2 L7 Q27 808 Z2 L7 Q28 809 Z2 L7 Q29 810 Z2 L7 Q30 811 Z2 L7 Q31 812 Z2 L7 Q32 813 Z2 L7 Q33 814 Z2 L7 Q34 815 Z2 L7 Q35 816 Z2 L7 Q36 817 Z2 L7 Q37 818 Z2 L7 Q38 819 Z2 L7 Q39 820 Z2 L8 Q1 821 Z2 L8 Q2 822 Z2 L8 Q3 823 Z2 L8 Q4 824 Z2 L8 Q5 825 Z2 L8 Q6 826 Z2 L8 Q7 827 Z2 L8 Q8 828 Z2 L8 Q9 829 Z2 L8 Q10 830 Z2 L8 Q11 831 Z2 L8 Q12 832 Z2 L8 Q13 833 Z2 L8 Q14 834 Z2 L8 Q15 835 Z2 L8 Q16 836 Z2 L8 Q17 837 Z2 L8 Q18 833 Z2 L8 Q19 839 Z2 L8 Q20 840 Z2 L8 Q21 841 Z2 L8 Q22 842 Z2 L8 Q23 843 Z2 L8 Q24 844 Z2 L8 Q25 845 Z2 L8 Q26 846 Z2 L8 Q27 847 Z2 L8 Q28 848 Z2 L8 Q29 849 Z2 L8 Q30 850 Z2 L8 Q31 851 Z2 L8 Q32 852 Z2 L8 Q33 853 Z2 L8 Q34 854 Z2 L8 Q35 855 Z2 L8 Q36 856 Z2 L8 Q37 857 Z2 L8 Q38 858 Z2 L8 Q39 859 Z2 L9 Q1 860 Z2 L9 Q2 861 Z2 L9 Q3 862 Z2 L9 Q4 863 Z2 L9 Q5 864 Z2 L9 Q6 865 Z2 L9 Q7 866 Z2 L9 Q8 867 Z2 L9 Q9 868 Z2 L9 Q10 869 Z2 L9 Q11 870 Z2 L9 Q12 871 Z2 L9 Q13 872 Z2 L9 Q14 873 Z2 L9 Q15 874 Z2 L9 Q16 875 Z2 L9 Q17 876 Z2 L9 Q18 877 Z2 L9 Q19 878 Z2 L9 Q20 879 Z2 L9 Q21 880 Z2 L9 Q22 881 Z2 L9 Q23 882 Z2 L9 Q24 883 Z2 L9 Q25 884 Z2 L9 Q26 885 Z2 L9 Q27 886 Z2 L9 Q28 887 Z2 L9 Q29 888 Z2 L9 Q30 889 Z2 L9 Q31 890 Z2 L9 Q32 891 Z2 L9 Q33 892 Z2 L9 Q34 893 Z2 L9 Q35 894 Z2 L9 Q36 895 Z2 L9 Q37 896 Z2 L9 Q38 897 Z2 L9 Q39 898 Z2 L10 Q1 899 Z2 L10 Q2 900 Z2 L10 Q3 901 Z2 L10 Q4 902 Z2 L10 Q5 903 Z2 L10 Q6 904 Z2 L10 Q7 905 Z2 L10 Q8 906 Z2 L10 Q9 907 Z2 L10 Q10 908 Z2 L10 Q11 909 Z2 L10 Q12 910 Z2 L10 Q13 911 Z2 L10 Q14 912 Z2 L10 Q15 913 Z2 L10 Q16 914 Z2 L10 Q17 915 Z2 L10 Q18 916 Z2 L10 Q19 917 Z2 L10 Q20 918 Z2 L10 Q21 919 Z2 L10 Q22 920 Z2 L10 Q23 921 Z2 L10 Q24 922 Z2 L10 Q25 923 Z2 L10 Q26 924 Z2 L10 Q27 925 Z2 L10 Q28 926 Z2 L10 Q29

TABLE 1-8  927 Z2 L10 Q30  928 Z2 L10 Q31  929 Z2 L10 Q32  930 Z2 L10 Q33  931 Z2 L10 Q34  932 Z2 L10 Q35  933 Z2 L10 Q36  934 Z2 L10 Q37  935 Z2 L10 Q38  936 Z2 L10 Q39  937 Z2 L11 Q1  938 Z2 L11 Q2  939 Z2 L11 Q3  940 Z2 L11 Q4  941 Z2 L11 Q5  942 Z2 L11 Q6  943 Z2 L11 Q7  944 Z2 L11 Q8  945 Z2 L11 Q9  946 Z2 L11 Q10  947 Z2 L11 Q11  948 Z2 L11 Q12  949 Z2 L11 Q13  950 Z2 L11 Q14  951 Z2 L11 Q15  952 Z2 L11 Q16  953 Z2 L11 Q17  954 Z2 L11 Q18  955 Z2 L11 Q19  956 Z2 L11 Q20  957 Z2 L11 Q21  958 Z2 L11 Q22  959 Z2 L11 Q23  960 Z2 L11 Q24  961 Z2 L11 Q25  962 Z2 L11 Q26  963 Z2 L11 Q27  964 Z2 L11 Q28  965 Z2 L11 Q29  966 Z2 L11 Q30  967 Z2 L11 Q31  968 Z2 L11 Q32  969 Z2 L11 Q33  970 Z2 L11 Q34  971 Z2 L11 Q35  972 Z2 L11 Q36  973 Z2 L11 Q37  974 Z2 L11 Q38  975 Z2 L11 Q39  976 Z2 L12 Q1  977 Z2 L12 Q2  978 Z2 L12 Q3  979 Z2 L12 Q4  980 Z2 L12 Q5  981 Z2 L12 Q6  982 Z2 L12 Q7  983 Z2 L12 Q8  984 Z2 L12 Q9  985 Z2 L12 Q10  986 Z2 L12 Q11  987 Z2 L12 Q12  988 Z2 L12 Q13  989 Z2 L12 Q14  990 Z2 L12 Q15  991 Z2 L12 Q16  992 Z2 L12 Q17  993 Z2 L12 Q18  994 Z2 L12 Q19  995 Z2 L12 Q20  996 Z2 L12 Q21  997 Z2 L12 Q22  998 Z2 L12 Q23  999 Z2 L12 Q24 1000 Z2 L12 Q25 1001 Z2 L12 Q26 1002 Z2 L12 Q27 1003 Z2 L12 Q28 1004 Z2 L12 Q29 1005 Z2 L12 Q30 1006 Z2 L12 Q31 1007 Z2 L12 Q32 1008 Z2 L12 Q33 1009 Z2 L12 Q34 1010 Z2 L12 Q35 1011 Z2 L12 Q36 1012 Z2 L12 Q37 1013 Z2 L12 Q38 1014 Z2 L12 Q39 1015 Z2 L13 Q1 1016 Z2 L13 Q2 1017 Z2 L13 Q3 1018 Z2 L13 Q4 1019 Z2 L13 Q5 1020 Z2 L13 Q6 1021 Z2 L13 Q7 1022 Z2 L13 Q8 1023 Z2 L13 Q9 1024 Z2 L13 Q10 1025 Z2 L13 Q11 1026 Z2 L13 Q12 1027 Z2 L13 Q13 1028 Z2 L13 Q14 1029 Z2 L13 Q15 1030 Z2 L13 Q16 1031 Z2 L13 Q17 1032 Z2 L13 Q18 1033 Z2 L13 Q19 1034 Z2 L13 Q20 1035 Z2 L13 Q21 1036 Z2 L13 Q22 1037 Z2 L13 Q23 1038 Z2 L13 Q24 1039 Z2 L13 Q25 1040 Z2 L13 Q26 1041 Z2 L13 Q27 1042 Z2 L13 Q28 1043 Z2 L13 Q29 1044 Z2 L13 Q30 1045 Z2 L13 Q31 1046 Z2 L13 Q32 1047 Z2 L13 Q33 1048 Z2 L13 Q34 1049 Z2 L13 Q35 1050 Z2 L13 Q36 1051 Z2 L13 Q37 1052 Z2 L13 Q38 1053 Z2 L13 Q39 1054 Z2 L14 Q1 1055 Z2 L14 Q2 1056 Z2 L14 Q3 1057 Z2 L14 Q4 1058 Z2 L14 Q5 1059 Z2 L14 Q6 1060 Z2 L14 Q7 1061 Z2 L14 Q8 1062 Z2 L14 Q9 1063 Z2 L14 Q10 1064 Z2 L14 Q11 1065 Z2 L14 Q12 1066 Z2 L14 Q13 1067 Z2 L14 Q14

TABLE 1-9 1068 Z2 L14 Q15 1069 Z2 L14 Q16 1070 Z2 L14 Q17 1071 Z2 L14 Q18 1072 Z2 L14 Q19 1073 Z2 L14 Q20 1074 Z2 L14 Q21 1075 Z2 L14 Q22 1076 Z2 L14 Q23 1077 Z2 L14 Q24 1078 Z2 L14 Q25 1079 Z2 L14 Q26 1080 Z2 L14 Q27 1081 Z2 L14 Q28 1082 Z2 L14 Q29 1083 Z2 L14 Q30 1084 Z2 L14 Q31 1085 Z2 L14 Q32 1086 Z2 L14 Q33 1087 Z2 L14 Q34 1088 Z2 L14 Q35 1089 Z2 L14 Q36 1090 Z2 L14 Q37 1091 Z2 L14 Q38 1092 Z2 L14 Q39 1093 Z3 L1 Q1 1094 Z3 L1 Q2 1095 Z3 L1 Q3 1096 Z3 L1 Q4 1097 Z3 L1 Q5 1098 Z3 L1 Q6 1099 Z3 L1 Q7 1100 Z3 L1 Q8 1101 Z3 L1 Q9 1102 Z3 L1 Q10 1103 Z3 L1 Q11 1104 Z3 L1 Q12 1105 Z3 L1 Q13 1106 Z3 L1 Q14 1107 Z3 L1 Q15 1108 Z3 L1 Q16 1109 Z3 L1 Q17 1110 Z3 L1 Q18 1111 Z3 L1 Q19 1112 Z3 L1 Q20 1113 Z3 L1 Q21 1114 Z3 L1 Q22 1115 Z3 L1 Q23 1116 Z3 L1 Q24 1117 Z3 L1 Q25 1118 Z3 L1 Q26 1119 Z3 L1 Q27 1120 Z3 L1 Q28 1121 Z3 L1 Q29 1122 Z3 L1 Q30 1123 Z3 L1 Q31 1124 Z3 L1 Q32 1125 Z3 L1 Q33 1126 Z3 L1 Q34 1127 Z3 L1 Q35 1128 Z3 L1 Q36 1129 Z3 L1 Q37 1130 Z3 L1 Q38 1131 Z3 L1 Q39 1132 Z3 L2 Q1 1133 Z3 L2 Q2 1134 Z3 L2 Q3 1135 Z3 L2 Q4 1136 Z3 L2 Q5 1137 Z3 L2 Q6 1138 Z3 L2 Q7 1139 Z3 L2 Q8 1140 Z3 L2 Q9 1141 Z3 L2 Q10 1142 Z3 L2 Q11 1143 Z3 L2 Q12 1144 Z3 L2 Q13 1145 Z3 L2 Q14 1146 Z3 L2 Q15 1147 Z3 L2 Q16 1148 Z3 L2 Q17 1149 Z3 L2 Q18 1150 Z3 L2 Q19 1151 Z3 L2 Q20 1152 Z3 L2 Q21 1153 Z3 L2 Q22 1154 Z3 L2 Q23 1155 Z3 L2 Q24 1156 Z3 L2 Q25 1157 Z3 L2 Q26 1158 Z3 L2 Q27 1159 Z3 L2 Q28 1160 Z3 L2 Q29 1161 Z3 L2 Q30 1162 Z3 L2 Q31 1163 Z3 L2 Q32 1164 Z3 L2 Q33 1165 Z3 L2 Q34 1166 Z3 L2 Q35 1167 Z3 L2 Q36 1168 Z3 L2 Q37 1169 Z3 L2 Q38 1170 Z3 L2 Q39 1171 Z3 L3 Q1 1172 Z3 L3 Q2 1173 Z3 L3 Q3 1174 Z3 L3 Q4 1175 Z3 L3 Q5 1176 Z3 L3 Q6 1177 Z3 L3 Q7 1178 Z3 L3 Q8 1179 Z3 L3 Q9 1180 Z3 L3 Q10 1181 Z3 L3 Q11 1182 Z3 L3 Q12 1183 Z3 L3 Q13 1184 Z3 L3 Q14 1185 Z3 L3 Q15 1186 Z3 L3 Q16 1187 Z3 L3 Q17 1188 Z3 L3 Q18 1189 Z3 L3 Q19 1190 Z3 L3 Q20 1191 Z3 L3 Q21 1192 Z3 L3 Q22 1193 Z3 L3 Q23 1194 Z3 L3 Q24 1195 Z3 L3 Q25 1196 Z3 L3 Q26 1197 Z3 L3 Q27 1198 Z3 L3 Q28 1199 Z3 L3 Q29 1200 Z3 L3 Q30 1201 Z3 L3 Q31 1202 Z3 L3 Q32 1203 Z3 L3 Q33 1204 Z3 L3 Q34 1205 Z3 L3 Q35 1206 Z3 L3 Q36 1207 Z3 L3 Q37 1208 Z3 L3 Q38

TABLE 1-10 1209 Z3 L3 Q39 1210 Z3 L4 Q1 1211 Z3 L4 Q2 1212 Z3 L4 Q3 1213 Z3 L4 Q4 1214 Z3 L4 Q5 1215 Z3 L4 Q6 1216 Z3 L4 Q7 1217 Z3 L4 Q8 1218 Z3 L4 Q9 1219 Z3 L4 Q10 1220 Z3 L4 Q11 1221 Z3 L4 Q12 1222 Z3 L4 Q13 1223 Z3 L4 Q14 1224 Z3 L4 Q15 1225 Z3 L4 Q16 1226 Z3 L4 Q17 1227 Z3 L4 Q18 1228 Z3 L4 Q19 1229 Z3 L4 Q20 1230 Z3 L4 Q21 1231 Z3 L4 Q22 1232 Z3 L4 Q23 1233 Z3 L4 Q24 1234 Z3 L4 Q25 1235 Z3 L4 Q26 1236 Z3 L4 Q27 1237 Z3 L4 Q28 1238 Z3 L4 Q29 1239 Z3 L4 Q30 1240 Z3 L4 Q31 1241 Z3 L4 Q32 1242 Z3 L4 Q33 1243 Z3 L4 Q34 1244 Z3 L4 Q35 1245 Z3 L4 Q36 1246 Z3 L4 Q37 1247 Z3 L4 Q38 1248 Z3 L4 Q39 1249 Z3 L5 Q1 1250 Z3 L5 Q2 1251 Z3 L5 Q3 1252 Z3 L5 Q4 1253 Z3 L5 Q5 1254 Z3 L5 Q6 1255 Z3 L5 Q7 1256 Z3 L5 Q8 1257 Z3 L5 Q9 1258 Z3 L5 Q10 1259 Z3 L5 Q11 1260 Z3 L5 Q12 1261 Z3 L5 Q13 1262 Z3 L5 Q14 1263 Z3 L5 Q15 1264 Z3 L5 Q16 1265 Z3 L5 Q17 1266 Z3 L5 Q18 1267 Z3 L5 Q19 1268 Z3 L5 Q20 1269 Z3 L5 Q21 1270 Z3 L5 Q22 1271 Z3 L5 Q23 1272 Z3 L5 Q24 1273 Z3 L5 Q25 1274 Z3 L5 Q26 1275 Z3 L5 Q27 1276 Z3 L5 Q28 1277 Z3 L5 Q29 1278 Z3 L5 Q30 1279 Z3 L5 Q31 1280 Z3 L5 Q32 1281 Z3 L5 Q33 1282 Z3 L5 Q34 1283 Z3 L5 Q35 1284 Z3 L5 Q36 1285 Z3 L5 Q37 1286 Z3 L5 Q38 1287 Z3 L5 Q39 1288 Z3 L6 Q1 1289 Z3 L6 Q2 1290 Z3 L6 Q3 1291 Z3 L6 Q4 1292 Z3 L6 Q5 1293 Z3 L6 Q6 1294 Z3 L6 Q7 1295 Z3 L6 Q8 1296 Z3 L6 Q9 1297 Z3 L6 Q10 1298 Z3 L6 Q11 1299 Z3 L6 Q12 1300 Z3 L6 Q13 1301 Z3 L6 Q14 1302 Z3 L6 Q15 1303 Z3 L6 Q16 1304 Z3 L6 Q17 1305 Z3 L6 Q18 1306 Z3 L6 Q19 1307 Z3 L6 Q20 1308 Z3 L6 Q21 1309 Z3 L6 Q22 1310 Z3 L6 Q23 1311 Z3 L6 Q24 1312 Z3 L6 Q25 1313 Z3 L6 Q26 1314 Z3 L6 Q27 1315 Z3 L6 Q28 1316 Z3 L6 Q29 1317 Z3 L6 Q30 1318 Z3 L6 Q31 1319 Z3 L6 Q32 1320 Z3 L6 Q33 1321 Z3 L6 Q34 1322 Z3 L6 Q35 1323 Z3 L6 Q36 1324 Z3 L6 Q37 1325 Z3 L6 Q38 1326 Z3 L6 Q39 1327 Z3 L7 Q1 1328 Z3 L7 Q2 1329 Z3 L7 Q3 1330 Z3 L7 Q4 1331 Z3 L7 Q5 1332 Z3 L7 Q6 1333 Z3 L7 Q7 1334 Z3 L7 Q8 1335 Z3 L7 Q9 1336 Z3 L7 Q10 1337 Z3 L7 Q11 1338 Z3 L7 Q12 1339 Z3 L7 Q13 1340 Z3 L7 Q14 1341 Z3 L7 Q15 1342 Z3 L7 Q16 1343 Z3 L7 Q17 1344 Z3 L7 Q18 1345 Z3 L7 Q19 1346 Z3 L7 Q20 1347 Z3 L7 Q21 1348 Z3 L7 Q22 1349 Z3 L7 Q23

TABLE 1-11 1350 Z3 L7 Q24 1351 Z3 L7 Q25 1352 Z3 L7 Q26 1353 Z3 L7 Q27 1354 Z3 L7 Q28 1355 Z3 L7 Q29 1356 Z3 L7 Q30 1357 Z3 L7 Q31 1358 Z3 L7 Q32 1359 Z3 L7 Q33 1360 Z3 L7 Q34 1361 Z3 L7 Q35 1362 Z3 L7 Q36 1363 Z3 L7 Q37 1364 Z3 L7 Q38 1365 Z3 L7 Q39 1366 Z3 L8 Q1 1367 Z3 L8 Q2 1368 Z3 L8 Q3 1369 Z3 L8 Q4 1370 Z3 L8 Q5 1371 Z3 L8 Q6 1372 Z3 L8 Q7 1373 Z3 L8 Q8 1374 Z3 L8 Q9 1375 Z3 L8 Q10 1376 Z3 L8 Q11 1377 Z3 L8 Q12 1378 Z3 L8 Q13 1379 Z3 L8 Q14 1380 Z3 L8 Q15 1381 Z3 L8 Q16 1382 Z3 L8 Q17 1383 Z3 L8 Q18 1384 Z3 L8 Q19 1385 Z3 L8 Q20 1386 Z3 L8 Q21 1387 Z3 L8 Q22 1388 Z3 L8 Q23 1389 Z3 L8 Q24 1390 Z3 L8 Q25 1391 Z3 L8 Q26 1392 Z3 L8 Q27 1393 Z3 L8 Q28 1394 Z3 L8 Q29 1395 Z3 L8 Q30 1396 Z3 L8 Q31 1397 Z3 L8 Q32 1398 Z3 L8 Q33 1399 Z3 L8 Q34 1400 Z3 L8 Q35 1401 Z3 L8 Q36 1402 Z3 L8 Q37 1403 Z3 L8 Q38 1404 Z3 L8 Q39 1405 Z3 L9 Q1 1406 Z3 L9 Q2 1407 Z3 L9 Q3 1408 Z3 L9 Q4 1409 Z3 L9 Q5 1410 Z3 L9 Q6 1411 Z3 L9 Q7 1412 Z3 L9 Q8 1413 Z3 L9 Q9 1414 Z3 L9 Q10 1415 Z3 L9 Q11 1416 Z3 L9 Q12 1417 Z3 L9 Q13 1418 Z3 L9 Q14 1419 Z3 L9 Q15 1420 Z3 L9 Q16 1421 Z3 L9 Q17 1422 Z3 L9 Q18 1423 Z3 L9 Q19 1424 Z3 L9 Q20 1425 Z3 L9 Q21 1426 Z3 L9 Q22 1427 Z3 L9 Q23 1428 Z3 L9 Q24 1429 Z3 L9 Q25 1430 Z3 L9 Q26 1431 Z3 L9 Q27 1432 Z3 L9 Q28 1433 Z3 L9 Q29 1434 Z3 L9 Q30 1435 Z3 L9 Q31 1436 Z3 L9 Q32 1437 Z3 L9 Q33 1438 Z3 L9 Q34 1439 Z3 L9 Q35 1440 Z3 L9 Q36 1441 Z3 L9 Q37 1442 Z3 L9 Q38 1443 Z3 L9 Q39 1444 Z3 L10 Q1 1445 Z3 L10 Q2 1446 Z3 L10 Q3 1447 Z3 L10 Q4 1448 Z3 L10 Q5 1449 Z3 L10 Q6 1450 Z3 L10 Q7 1451 Z3 L10 Q8 1452 Z3 L10 Q9 1453 Z3 L10 Q10 1454 Z3 L10 Q11 1455 Z3 L10 Q12 1456 Z3 L10 Q13 1457 Z3 L10 Q14 1458 Z3 L10 Q15 1459 Z3 L10 Q16 1460 Z3 L10 Q17 1461 Z3 L10 Q18 1462 Z3 L10 Q19 1463 Z3 L10 Q20 1464 Z3 L10 Q21 1465 Z3 L10 Q22 1466 Z3 L10 Q23 1467 Z3 L10 Q24 1468 Z3 L10 Q25 1469 Z3 L10 Q26 1470 Z3 L10 Q27 1471 Z3 L10 Q28 1472 Z3 L10 Q29 1473 Z3 L10 Q30 1474 Z3 L10 Q31 1475 Z3 L10 Q32 1476 Z3 L10 Q33 1477 Z3 L10 Q34 1478 Z3 L10 Q35 1479 Z3 L10 Q36 1480 Z3 L10 Q37 1481 Z3 L10 Q38 1482 Z3 L10 Q39 1483 Z3 L11 Q1 1484 Z3 L11 Q2 1485 Z3 L11 Q3 1486 Z3 L11 Q4 1487 Z3 L11 Q5 1488 Z3 L11 Q6 1489 Z3 L11 Q7 1490 Z3 L11 Q8

TABLE 1-12 1491 Z3 L11 Q9 1492 Z3 L11 Q10 1493 Z3 L11 Q11 1494 Z3 L11 Q12 1495 Z3 L11 Q13 1496 Z3 L11 Q14 1497 Z3 L11 Q15 1498 Z3 L11 Q16 1499 Z3 L11 Q17 1500 Z3 L11 Q18 1501 Z3 L11 Q19 1502 Z3 L11 Q20 1503 Z3 L11 Q21 1504 Z3 L11 Q22 1505 Z3 L11 Q23 1506 Z3 L11 Q24 1507 Z3 L11 Q25 1508 Z3 L11 Q26 1509 Z3 L11 Q27 1510 Z3 L11 Q28 1511 Z3 L11 Q29 1512 Z3 L11 Q30 1513 Z3 L11 Q31 1514 Z3 L11 Q32 1515 Z3 L11 Q33 1516 Z3 L11 Q34 1517 Z3 L11 Q35 1518 Z3 L11 Q36 1519 Z3 L11 Q37 1520 Z3 L11 Q38 1521 Z3 L11 Q39 1522 Z3 L12 Q1 1523 Z3 L12 Q2 1524 Z3 L12 Q3 1525 Z3 L12 Q4 1526 Z3 L12 Q5 1527 Z3 L12 Q6 1528 Z3 L12 Q7 1529 Z3 L12 Q8 1530 Z3 L12 Q9 1531 Z3 L12 Q10 1532 Z3 L12 Q11 1533 Z3 L12 Q12 1534 Z3 L12 Q13 1535 Z3 L12 Q14 1536 Z3 L12 Q15 1537 Z3 L12 Q16 1538 Z3 L12 Q17 1539 Z3 L12 Q18 1540 Z3 L12 Q19 1541 Z3 L12 Q20 1542 Z3 L12 Q21 1543 Z3 L12 Q22 1544 Z3 L12 Q23 1545 Z3 L12 Q24 1546 Z3 L12 Q25 1547 Z3 L12 Q26 1548 Z3 L12 Q27 1549 Z3 L12 Q28 1550 Z3 L12 Q29 1551 Z3 L12 Q30 1552 Z3 L12 Q31 1553 Z3 L12 Q32 1554 Z3 L12 Q33 1555 Z3 L12 Q34 1556 Z3 L12 Q35 1557 Z3 L12 Q36 1558 Z3 L12 Q37 1559 Z3 L12 Q38 1560 Z3 L12 Q39 1561 Z3 L13 Q1 1562 Z3 L13 Q2 1563 Z3 L13 Q3 1564 Z3 L13 Q4 1565 Z3 L13 Q5 1566 Z3 L13 Q6 1567 Z3 L13 Q7 1568 Z3 L13 Q8 1569 Z3 L13 Q9 1570 Z3 L13 Q10 1571 Z3 L13 Q11 1572 Z3 L13 Q12 1573 Z3 L13 Q13 1574 Z3 L13 Q14 1575 Z3 L13 Q15 1576 Z3 L13 Q16 1577 Z3 L13 Q17 1578 Z3 L13 Q18 1579 Z3 L13 Q19 1580 Z3 L13 Q20 1581 Z3 L13 Q21 1582 Z3 L13 Q22 1583 Z3 L13 Q23 1584 Z3 L13 Q24 1585 Z3 L13 Q25 1586 Z3 L13 Q26 1587 Z3 L13 Q27 1588 Z3 L13 Q28 1589 Z3 L13 Q29 1590 Z3 L13 Q30 1591 Z3 L13 Q31 1592 Z3 L13 Q32 1593 Z3 L13 Q33 1594 Z3 L13 Q34 1595 Z3 L13 Q35 1596 Z3 L13 Q36 1597 Z3 L13 Q37 1598 Z3 L13 Q38 1599 Z3 L13 Q39 1600 Z3 L14 Q1 1601 Z3 L14 Q2 1602 Z3 L14 Q3 1603 Z3 L14 Q4 1604 Z3 L14 Q5 1605 Z3 L14 Q6 1606 Z3 L14 Q7 1607 Z3 L14 Q8 1608 Z3 L14 Q9 1609 Z3 L14 Q10 1610 Z3 L14 Q11 1 13 Z3 L14 Q12 1612 Z3 L14 Q13 1613 Z3 L14 Q14 1614 Z3 L14 Q15 1615 Z3 L14 Q16 1616 Z3 L14 Q17 1617 Z3 L14 Q18 1618 Z3 L14 Q19 1619 Z3 L14 Q20 1620 Z3 L14 Q21 1621 Z3 L14 Q22 1 73 Z3 L14 Q23 1623 Z3 L14 Q24 1624 Z3 L14 Q25 1625 Z3 L14 Q26 1626 Z3 L14 Q27 1627 Z3 L14 Q28 1628 Z3 L14 Q29 1629 Z3 L14 Q30 1630 Z3 L14 Q31 1631 Z3 L14 Q32

TABLE 1-13 1632 Z3 L14 Q33 1633 Z3 L14 Q34 1634 Z3 L14 Q35 1635 Z3 L14 Q36 1636 Z3 L14 Q37 1637 Z3 L14 Q38 1638 Z3 L14 Q39 1639 Z4 L1 Q1 1640 Z4 L1 Q2 1641 Z4 L1 Q3 1642 Z4 L1 Q4 1643 Z4 L1 Q5 1644 Z4 L1 Q6 1645 Z4 L1 Q7 1646 Z4 L1 Q8 1647 Z4 L1 Q9 1648 Z4 L1 Q10 1649 Z4 L1 Q11 1650 Z4 L1 Q12 1651 Z4 L1 Q13 1652 Z4 L1 Q14 1653 Z4 L1 Q15 1654 Z4 L1 Q16 1655 Z4 L1 Q17 1656 Z4 L1 Q18 1657 Z4 L1 Q19 1658 Z4 L1 Q20 1659 Z4 L1 Q21 1660 Z4 L1 Q22 1661 Z4 L1 Q23 1662 Z4 L1 Q24 1663 Z4 L1 Q25 1664 Z4 L1 Q26 1665 Z4 L1 Q27 1666 Z4 L1 Q28 1667 Z4 L1 Q29 1668 Z4 L1 Q30 1669 Z4 L1 Q31 1670 Z4 L1 Q32 1671 Z4 L1 Q33 1672 Z4 L1 Q34 1573 Z4 L1 Q35 1674 Z4 L1 Q36 1675 Z4 L1 Q37 1676 Z4 L1 Q38 1677 Z4 L1 Q39 1678 Z4 L2 Q1 1679 Z4 L2 Q2 1680 Z4 L2 Q3 1681 Z4 L2 Q4 1682 Z4 L2 Q5 1683 Z4 L2 Q6 1584 Z4 L2 Q7 1685 Z4 L2 Q8 1636 Z4 L2 Q9 1687 Z4 L2 Q10 1688 Z4 L2 Q11 1689 Z4 L2 Q12 1690 Z4 L2 Q13 1691 Z4 L2 Q14 1692 Z4 L2 Q15 1693 Z4 L2 Q16 1694 Z4 L2 Q17 1695 Z4 L2 Q18 1696 Z4 L2 Q19 1697 Z4 L2 Q20 1698 Z4 L2 Q21 1699 Z4 L2 Q22 1700 Z4 L2 Q23 1701 Z4 L2 Q24 1702 Z4 L2 Q25 1703 Z4 L2 Q25 1704 Z4 L2 Q27 1705 Z4 L2 Q28 1706 Z4 L2 Q29 1707 Z4 L2 Q30 1708 Z4 L2 Q31 1709 Z4 L2 Q32 1710 Z4 L2 Q33 1711 Z4 L2 Q34 1712 Z4 L2 Q35 1713 Z4 L2 Q36 1714 Z4 L2 Q37 1715 Z4 L2 Q38 1716 Z4 L2 Q39 1717 Z4 L3 Q1 1718 Z4 L3 Q2 1719 Z4 L3 Q3 1720 Z4 L3 Q4 1721 Z4 L3 Q5 1722 Z4 L3 Q6 1723 Z4 L3 Q7 1724 Z4 L3 Q8 1725 Z4 L3 Q9 1726 Z4 L3 Q10 1727 Z4 L3 Q11 1728 Z4 L3 Q12 1729 Z4 L3 Q13 1730 Z4 L3 Q14 1731 Z4 L3 Q15 1732 Z4 L3 Q16 1733 Z4 L3 Q17 1734 Z4 L3 Q18 1735 Z4 L3 Q19 1736 Z4 L3 Q20 1737 Z4 L3 Q21 1738 Z4 L3 Q22 1739 Z4 L3 Q23 1740 Z4 L3 Q24 1741 Z4 L3 Q25 1742 Z4 L3 Q26 1743 Z4 L3 Q27 1744 Z4 L3 Q28 1745 Z4 L3 Q29 1746 Z4 L3 Q30 1747 Z4 L3 Q31 1748 Z4 L3 Q32 1749 Z4 L3 Q33 1750 Z4 L3 Q34 1751 Z4 L3 Q35 1752 Z4 L3 Q36 1753 Z4 L3 Q37 1754 Z4 L3 Q38 1755 Z4 L3 Q39 1756 Z4 L4 Q1 1757 Z4 L4 Q2 1758 Z4 L4 Q3 1759 Z4 L4 Q4 1760 Z4 L4 Q5 1761 Z4 L4 Q6 1762 Z4 L4 Q7 1763 Z4 L4 Q8 1764 Z4 L4 Q9 1765 Z4 L4 Q10 1766 Z4 L4 Q11 1767 Z4 L4 Q12 1768 Z4 L4 Q13 1769 Z4 L4 Q14 1770 Z4 L4 Q15 1771 Z4 L4 Q16 1772 Z4 L4 Q17

TABLE 1-14 1773 Z4 L4 Q18 1774 Z4 L4 Q19 1775 Z4 L4 Q20 1776 Z4 L4 Q21 1777 Z4 L4 Q22 1778 Z4 L4 Q23 1779 Z4 L4 Q24 1780 Z4 L4 Q25 1781 Z4 L4 Q26 1782 Z4 L4 Q27 1783 Z4 L4 Q28 1784 Z4 L4 Q29 1785 Z4 L4 Q30 1786 Z4 L4 Q31 1787 Z4 L4 Q32 1738 Z4 L4 Q33 1789 Z4 L4 Q34 1790 Z4 L4 Q35 1791 Z4 L4 Q36 1792 Z4 L4 Q37 1793 Z4 L4 Q33 1794 Z4 L4 Q39 1795 Z4 L5 Q1 1796 Z4 L5 Q2 1797 Z4 L5 Q3 1798 Z4 L5 Q4 1799 Z4 L5 Q5 1800 Z4 L5 Q6 1801 Z4 L5 Q7 1802 Z4 L5 Q8 1803 Z4 L5 Q9 1804 Z4 L5 Q10 1805 Z4 L5 Q11 1806 Z4 L5 Q12 1807 Z4 L5 Q13 1808 Z4 L5 Q14 1809 Z4 L5 Q15 1810 Z4 L5 Q16 1811 Z4 L5 Q17 1812 Z4 L5 Q18 1813 Z4 L5 Q19 1814 Z4 L5 Q20 1815 Z4 L5 Q21 1816 Z4 L5 Q22 1817 Z4 L5 Q23 1818 Z4 L5 Q24 1819 Z4 L5 Q25 1820 Z4 L5 Q26 1821 Z4 L5 Q27 1822 Z4 L5 Q28 1823 Z4 L5 Q29 1824 Z4 L5 Q30 1825 Z4 L5 Q31 1826 Z4 L5 Q32 1827 Z4 L5 Q33 1828 Z4 L5 Q34 1829 Z4 L5 Q35 1830 Z4 L5 Q36 1831 Z4 L5 Q37 1832 Z4 L5 Q38 1833 Z4 L5 Q39 1834 Z4 L6 Q1 1835 Z4 L6 Q2 1836 Z4 L6 Q3 1837 Z4 L6 Q4 1838 Z4 L6 Q5 1839 Z4 L6 Q6 1840 Z4 L6 Q7 1841 Z4 L6 Q8 1842 Z4 L6 Q9 1843 Z4 L6 Q10 1844 Z4 L6 Q11 1845 Z4 L6 Q12 1846 Z4 L6 Q13 1847 Z4 L6 Q14 1848 Z4 L6 Q15 1849 Z4 L6 Q16 1850 Z4 L6 Q17 1851 Z4 L6 Q18 1852 Z4 L6 Q19 1853 Z4 L6 Q20 1854 Z4 L6 Q21 1855 Z4 L6 Q22 1856 Z4 L6 Q23 1857 Z4 L6 Q24 1858 Z4 L6 Q25 1859 Z4 L6 Q26 1860 Z4 L6 Q27 1861 Z4 L6 Q28 1862 Z4 L6 Q29 1863 Z4 L6 Q30 1864 Z4 L6 Q31 1865 Z4 L6 Q32 1866 Z4 L6 Q33 1867 Z4 L6 Q34 1868 Z4 L6 Q35 1869 Z4 L6 Q36 1870 Z4 L6 Q37 1871 Z4 L6 Q38 1872 Z4 L6 Q39 1873 Z4 L7 Q1 1874 Z4 L7 Q2 1875 Z4 L7 Q3 1876 Z4 L7 Q4 1877 Z4 L7 Q5 1878 Z4 L7 Q6 1879 Z4 L7 Q7 1880 Z4 L7 Q8 1881 Z4 L7 Q9 1882 Z4 L7 Q10 1883 Z4 L7 Q11 1884 Z4 L7 Q12 1885 Z4 L7 Q13 1886 Z4 L7 Q14 1887 Z4 L7 Q15 1888 Z4 L7 Q16 1889 Z4 L7 Q17 1890 Z4 L7 Q18 1891 Z4 L7 Q19 1892 Z4 L7 Q20 1893 Z4 L7 Q21 1894 Z4 L7 Q22 1895 Z4 L7 Q23 1896 Z4 L7 Q24 1897 Z4 L7 Q25 1898 Z4 L7 Q26 1899 Z4 L7 Q27 1900 Z4 L7 Q28 1901 Z4 L7 Q29 1902 Z4 L7 Q30 1903 Z4 L7 Q31 1904 Z4 L7 Q32 1905 Z4 L7 Q33 1906 Z4 L7 Q34 1907 Z4 L7 Q35 1908 Z4 L7 Q36 1909 Z4 L7 Q37 1910 Z4 L7 Q38 1911 Z4 L7 Q39 1912 Z4 L8 Q1 1913 Z4 L8 Q2

TABLE 15 1914 Z4 L8 Q3 1915 Z4 L8 Q4 1916 Z4 L8 Q5 1917 Z4 L8 Q6 1918 Z4 L8 Q7 1919 Z4 L8 Q8 1920 Z4 L8 Q9 1921 Z4 L8 Q10 1922 Z4 L8 Q11 1923 Z4 L8 Q12 1924 Z4 L8 Q13 1925 Z4 L8 Q14 1926 Z4 L8 Q15 1927 Z4 L8 Q16 1928 Z4 L8 Q17 1929 Z4 L8 Q18 1930 Z4 L8 Q19 1931 Z4 L8 Q20 1932 Z4 L8 Q21 1933 Z4 L8 Q22 1934 Z4 L8 Q23 1935 Z4 L8 Q24 1936 Z4 L8 Q25 1937 Z4 L8 Q26 1938 Z4 L8 Q27 1939 Z4 L8 Q28 1940 Z4 L8 Q29 1941 Z4 L8 Q30 1942 Z4 L8 Q31 1943 Z4 L8 Q32 1944 Z4 L8 Q33 1945 Z4 L8 Q34 1946 Z4 L8 Q35 1947 Z4 L8 Q36 1948 Z4 L8 Q37 1949 Z4 L8 Q38 1950 Z4 L8 Q39 1951 Z4 L9 Q1 1952 Z4 L9 Q2 1953 Z4 L9 Q3 1954 Z4 L9 Q4 1955 Z4 L9 Q5 1956 Z4 L9 Q6 1957 Z4 L9 Q7 1958 Z4 L9 Q8 1959 Z4 L9 Q9 1960 Z4 L9 Q10 1961 Z4 L9 Q11 1962 Z4 L9 Q12 1963 Z4 L9 Q13 1964 Z4 L9 Q14 1965 Z4 L9 Q15 1966 Z4 L9 Q16 1967 Z4 L9 Q17 1968 Z4 L9 Q18 1969 Z4 L9 Q19 1970 Z4 L9 Q20 1971 Z4 L9 Q21 1972 Z4 L9 Q22 1973 Z4 L9 Q23 1974 Z4 L9 Q24 1975 Z4 L9 Q25 1976 Z4 L9 Q26 1977 Z4 L9 Q27 1978 Z4 L9 Q28 1979 Z4 L9 Q29 1980 Z4 L9 Q30 1981 Z4 L9 Q31 1982 Z4 L9 Q32 1983 Z4 L9 Q33 1984 Z4 L9 Q34 1985 Z4 L9 Q35 1986 Z4 L9 Q36 1987 Z4 L9 Q37 1988 Z4 L9 Q38 1989 Z4 L9 Q39 1990 Z4 L10 Q1 1991 Z4 L10 Q2 1992 Z4 L10 Q3 1993 Z4 L10 Q4 1994 Z4 L10 Q5 1995 Z4 L10 Q6 1996 Z4 L10 Q7 1997 Z4 L10 Q8 1998 Z4 L10 Q9 1999 Z4 L10 Q10 2000 Z4 L10 Q11 2001 Z4 L10 Q12 2002 Z4 L10 Q13 2003 Z4 L10 Q14 2004 Z4 L10 Q15 2005 Z4 L10 Q16 2006 Z4 L10 Q17 2007 Z4 L10 Q18 2008 Z4 L10 Q19 2009 Z4 L10 Q20 2010 Z4 L10 Q21 2011 Z4 L10 Q22 2012 Z4 L10 Q23 2013 Z4 L10 Q24 2014 Z4 L10 Q25 2015 Z4 L10 Q26 2016 Z4 L10 Q27 2017 Z4 L10 Q28 2018 Z4 L10 Q29 2019 Z4 L10 Q30 2020 Z4 L10 Q31 2021 Z4 L10 Q32 2022 Z4 L10 Q33 2023 Z4 L10 Q34 2024 Z4 L10 Q35 2025 Z4 L10 Q36 2026 Z4 L10 Q37 2027 Z4 L10 Q36 2028 Z4 L10 Q39 2029 Z4 L11 Q1 2030 Z4 L11 Q2 2031 Z4 L11 Q3 2032 Z4 L11 Q4 2033 Z4 L11 Q5 2034 Z4 L11 Q6 2035 Z4 L11 Q7 2036 Z4 L11 Q8 2037 Z4 L11 Q9 2038 Z4 L11 Q10 2039 Z4 L11 Q11 2040 Z4 L11 Q12 2041 Z4 L11 Q13 2042 Z4 L11 Q14 2043 Z4 L11 Q15 2044 Z4 L11 Q16 2045 Z4 L11 Q17 2046 Z4 L11 Q18 2047 Z4 L11 Q19 2048 Z4 L11 Q20 2049 Z4 L11 Q21 2050 Z4 L11 Q22 2051 Z4 L11 Q23 2052 Z4 L11 Q24 2053 Z4 L11 Q25 2054 Z4 L11 Q26

2055 Z4 L11 Q27 2056 Z4 L11 Q28 2057 Z4 L11 Q29 2058 Z4 L11 Q30 2059 Z4 L11 Q31 2060 Z4 L11 Q32 2061 Z4 L11 Q33 2062 Z4 L11 Q34 2063 Z4 L11 Q35 2064 Z4 L11 Q36 2065 Z4 L11 Q37 2066 Z4 L11 Q38 2067 Z4 L11 Q39 2068 Z4 L12 Q1 2069 Z4 L12 Q2 2070 Z4 L12 Q3 2071 Z4 L12 Q4 2072 Z4 L12 Q5 2073 Z4 L12 Q6 2074 Z4 L12 Q7 2075 Z4 L12 Q8 2076 Z4 L12 Q9 2077 Z4 L12 Q10 2078 Z4 L12 Q11 2079 Z4 L12 Q12 2080 Z4 L12 Q13 2081 Z4 L12 Q14 2082 Z4 L12 Q15 2083 Z4 L12 Q16 2084 Z4 L12 Q17 2085 Z4 L12 Q18 2086 Z4 L12 Q19 2087 Z4 L12 Q20 2088 Z4 L12 Q21 2089 Z4 L12 Q22 2090 Z4 L12 Q23 2091 Z4 L12 Q24 2092 Z4 L12 Q25 2093 Z4 L12 Q26 2094 Z4 L12 Q27 2095 Z4 L12 Q28 2096 Z4 L12 Q29 2097 Z4 L12 Q30 2098 Z4 L12 Q31 2099 Z4 L12 Q32 2100 Z4 L12 Q33 2101 Z4 L12 Q34 2102 Z4 L12 Q35 2103 Z4 L12 Q36 2104 Z4 L12 Q37 2105 Z4 L12 Q38 2106 Z4 L12 Q39 2107 Z4 L13 Q1 2108 Z4 L13 Q2 2109 Z4 L13 Q3 2110 Z4 L13 Q4 2111 Z4 L13 Q5 2112 Z4 L13 Q6 2113 Z4 L13 Q7 2114 Z4 L13 Q8 2115 Z4 L13 Q9 2116 Z4 L13 Q10 2117 Z4 L13 Q11 2118 Z4 L13 Q12 2119 Z4 L13 Q13 2120 Z4 L13 Q14 2121 Z4 L13 Q15 2122 Z4 L13 Q16 2123 Z4 L13 Q17 2124 Z4 L13 Q18 2125 Z4 L13 Q19 2126 Z4 L13 Q20 2127 Z4 L13 Q21 2128 Z4 L13 Q22 2129 Z4 L13 Q23 2130 Z4 L13 Q24 2131 Z4 L13 Q25 2132 Z4 L13 Q26 2133 Z4 L13 Q27 2134 Z4 L13 Q28 2135 Z4 L13 Q29 2136 Z4 L13 Q30 2137 Z4 L13 Q31 2138 Z4 L13 Q32 2139 Z4 L13 Q33 2140 Z4 L13 Q34 2141 Z4 L13 Q35 2142 Z4 L13 Q36 2143 Z4 L13 Q37 2144 Z4 L13 Q38 2145 Z4 L13 Q39 2146 Z4 L14 Q1 2147 Z4 L14 Q2 2148 Z4 L14 Q3 2149 Z4 L14 Q4 2150 Z4 L14 Q5 2151 Z4 L14 Q6 2152 Z4 L14 Q7 2153 Z4 L14 Q8 2154 Z4 L14 Q9 2155 Z4 L14 Q10 2156 Z4 L14 Q11 2157 Z4 L14 Q12 2158 Z4 L14 Q13 2159 Z4 L14 Q14 2160 Z4 L14 Q15 2161 Z4 L14 Q16 2162 Z4 L14 Q17 2163 Z4 L14 Q18 2164 Z4 L14 Q19 2165 Z4 L14 Q20 2166 Z4 L14 Q21 2167 Z4 L14 Q22 2168 Z4 L14 Q23 2169 Z4 L14 Q24 2170 Z4 L14 Q25 2171 Z4 L14 Q26 2172 Z4 L14 Q27 2173 Z4 L14 Q28 2174 Z4 L14 Q29 2175 Z4 L14 Q30 2176 Z4 L14 Q31 2177 Z4 L14 Q32 2178 Z4 L14 Q33 2179 Z4 L14 Q34 2180 Z4 L14 Q35 2181 Z4 L14 Q36 2182 Z4 L14 Q37 2183 Z4 L14 Q38 2184 Z4 L14 Q39

TABLE 1-17 Example R^(ZL) L^(a) Q^(a) 2185 Z1 L1 Q40 2186 Z1 L1 Q41 2187 Z1 L1 Q42 2188 Z1 L1 Q43 2189 Z1 L1 Q44 2190 Z1 L1 Q45 2191 Z1 L1 Q46 2192 Z1 L1 Q47 2193 Z1 L1 Q48 2194 Z1 L1 Q49 2195 Z1 L1 Q50 2196 Z1 L1 Q51 2197 Z1 L1 Q52 2198 Z1 L1 Q53 2199 Z1 L1 Q54 2200 Z1 L1 Q55 2201 Z1 L1 Q56 2202 Z1 L1 Q57 2203 Z1 L1 Q58 2204 Z1 L1 Q59 2205 Z1 L1 Q60 2206 Z1 L1 Q61 2207 Z1 L1 Q62 2208 Z1 L1 Q63 2209 Z1 L1 Q64 2210 Z1 L1 Q65 2211 Z1 L1 Q66 2212 Z1 L1 Q67 2213 Z1 L1 Q68 2214 Z1 L1 Q69 2215 Z1 L1 Q70 2216 Z1 L1 Q71 2217 Z1 L1 Q72 2218 Z1 L1 Q73 2219 Z1 L1 Q74 2220 Z1 L1 Q75 2221 Z1 L1 Q76 2222 Z1 L1 Q77 2223 Z1 L1 Q78 2224 Z1 L1 Q79 2225 Z1 L1 Q80 2226 Z1 L1 Q81 2227 Z1 L1 Q82 2228 Z1 L1 Q83 2229 Z1 L1 Q84 2230 Z1 L1 Q85 2231 Z1 L1 Q86 2232 Z1 L1 Q87 2233 Z1 L1 Q88 2234 Z1 L1 Q89 2235 Z1 L1 Q90 2236 Z1 L1 Q91 2237 Z1 L1 Q92 2238 Z1 L1 Q93 2239 Z1 L1 Q94 2240 Z1 L1 Q95 2241 Z1 L1 Q96 2242 Z1 L1 Q97 2243 Z1 L1 Q98 2244 Z1 L1 Q99 2245 Z1 L1 Q100 2246 Z1 L1 Q101 2247 Z1 L1 Q102 2248 Z1 L1 Q103 2249 Z1 L1 Q40 2250 Z1 L2 Q41 2251 Z1 L2 Q42 2252 Z1 L2 Q43 2253 Z1 L2 Q44 2254 Z1 L2 Q45 2255 Z1 L2 Q46 2256 Z1 L2 Q47 2257 Z1 L2 Q48 2258 Z1 L2 Q49 2259 Z1 L2 Q50 2260 Z1 L2 Q51 2261 Z1 L2 Q52 2262 Z1 L2 Q53 2263 Z1 L2 Q54 2264 Z1 L2 Q55 2265 Z1 L2 Q56 2266 Z1 L2 Q57 2267 Z1 L2 Q58 2268 Z1 L2 Q59 2269 Z1 L2 Q60 2270 Z1 L2 Q61 2271 Z1 L2 Q62 2272 Z1 L2 Q63 2273 Z1 L2 Q64 2274 Z1 L2 Q65 2275 Z1 L2 Q66 2276 Z1 L2 Q67 2277 Z1 L2 Q68 2278 Z1 L2 Q69 2279 Z1 L2 Q70 2280 Z1 L2 Q71 2281 Z1 L2 Q72 2282 Z1 L2 Q73 2283 Z1 L2 Q74 2284 Z1 L2 Q75 2285 Z1 L2 Q76 2286 Z1 L2 Q77 2287 Z1 L2 Q78 2288 Z1 L2 Q79 2289 Z1 L2 Q80 2290 Z1 L2 Q81 2291 Z1 L2 Q82 2292 Z1 L2 Q83 2293 Z1 L2 Q84 2294 Z1 L2 Q85 2295 Z1 L2 Q86 2296 Z1 L2 Q87 2297 Z1 L2 Q88 2298 Z1 L2 Q89 2299 Z1 L2 Q90 2300 Z1 L2 Q91 2301 Z1 L2 Q92 2302 Z1 L2 Q93 2303 Z1 L2 Q94 2304 Z1 L2 Q95 2305 Z1 L2 Q96 2306 Z1 L2 Q97 2307 Z1 L2 Q98 2308 Z1 L2 Q99 2309 Z1 L2 Q100 2310 Z1 L2 Q101 2311 Z1 L2 Q102 2312 Z1 L2 Q103 2313 Z1 L2 Q40 2314 Z1 L3 Q41 2315 Z1 L3 Q42 2316 Z1 L3 Q43 2317 Z1 L3 4Q4 2318 Z1 L3 Q45 2319 Z1 L3 Q56 2320 Z1 L3 Q57 2321 Z1 L3 Q58 2322 Z1 L3 Q59 2323 Z1 L3 Q50 2324 Z1 L3 Q51 2325 Z1 L3 Q52 2326 Z1 L3 Q53 2327 Z1 L3 Q54 2328 Z1 L3 Q55 2329 Z1 L3 Q56 2330 Z1 L3 Q57 2331 Z1 L3 Q58 2332 Z1 L3 Q59 2333 Z1 L3 Q60 2334 Z1 L3 Q61 2335 Z1 L3 Q62 2336 Z1 L3 Q63 2337 Z1 L3 Q64 2338 Z1 L3 Q65 2339 Z1 L3 Q66 2340 Z1 L3 Q67 2341 Z1 L3 Q68 2342 Z1 L3 Q69 2343 Z1 L3 Q70 2344 Z1 L3 Q71 2345 Z1 L3 Q72 2346 Z1 L3 Q73 2347 Z1 L3 Q74 2348 Z1 L3 Q75 2349 Z1 L3 Q76 2350 Z1 L3 Q77 2351 Z1 L3 Q78 2352 Z1 L3 Q79 2353 Z1 L3 Q80 2354 Z1 L3 Q81 2355 Z1 L3 Q82 2356 Z1 L3 Q83 2357 Z1 L3 Q84 2358 Z1 L3 Q85 2359 Z1 L3 Q86 2360 Z1 L3 Q87 2361 Z1 L3 Q88 2362 Z1 L3 Q89 2363 Z1 L3 Q90 2364 Z1 L3 Q91 2365 Z1 L3 Q92 2366 Z1 L3 Q93 2367 Z1 L3 Q94 2368 Z1 L3 Q95 2369 Z1 L3 Q96 2370 Z1 L3 Q97 2371 Z1 L3 Q98 2372 Z1 L3 Q99 2373 Z1 L3 Q100 2374 Z1 L3 Q101 2375 Z1 L3 Q102 2376 Z1 L3 Q103 2377 Z1 L4 Q40 2378 Z1 L4 Q41 2379 Z1 L4 Q42 2380 Z1 L4 Q43 2381 Z1 L4 Q44 2382 Z1 L4 Q45 2383 Z1 L4 Q46 2384 Z1 L4 Q47

TABLE 1-18 2385 Z1 L4 Q48 2386 Z1 L4 Q49 2387 Z1 L4 Q50 2388 Z1 L4 Q51 2389 Z1 L4 Q52 2390 Z1 L4 Q53 2391 Z1 L4 Q54 2392 Z1 L4 Q55 2393 Z1 L4 Q56 2394 Z1 L4 Q57 2395 Z1 L4 Q58 2396 Z1 L4 Q59 2397 Z1 L4 Q60 2398 Z1 L4 Q61 2399 Z1 L4 Q62 2400 Z1 L4 Q63 2401 Z1 L4 Q64 2402 Z1 L4 Q65 2403 Z1 L4 Q66 2404 Z1 L4 Q67 2405 Z1 L4 Q68 2406 Z1 L4 Q69 2407 Z1 L4 Q70 2408 Z1 L4 Q71 2409 Z1 L4 Q72 2410 Z1 L4 Q73 2411 Z1 L4 Q74 2412 Z1 L4 Q75 2413 Z1 L4 Q76 2414 Z1 L4 Q77 2415 Z1 L4 Q78 2416 Z1 L4 Q79 2417 Z1 L4 Q80 2418 Z1 L4 Q81 2419 Z1 L4 Q82 2420 Z1 L4 Q83 2421 Z1 L4 Q84 2422 Z1 L4 Q85 2423 Z1 L4 Q86 2424 Z1 L4 Q87 2425 Z1 L4 Q88 2426 Z1 L4 Q89 2427 Z1 L4 Q90 2428 Z1 L4 Q91 2429 Z1 L4 Q92 2430 Z1 L4 Q93 2431 Z1 L4 Q94 3432 Z1 L4 Q95 2433 Z1 L4 Q96 2434 Z1 L4 Q97 2435 Z1 L4 Q98 2436 Z1 L4 Q99 2437 Z1 L4 Q100 2438 Z1 L4 Q101 2439 Z1 L4 Q102 2440 Z1 L4 Q103 2441 Z1 L5 Q40 2442 Z1 L5 Q41 2443 Z1 L5 Q42 2444 Z1 L5 Q43 2445 Z1 L5 Q44 2446 Z1 L5 Q45 2447 Z1 L5 Q46 2448 Z1 L5 Q47 2449 Z1 L5 Q48 2450 Z1 L5 Q49 2451 Z1 L5 Q50 2452 Z1 L5 Q51 2453 Z1 L5 Q52 2454 Z1 L5 Q53 2455 Z1 L5 Q54 2456 Z1 L5 Q55 2457 Z1 L5 Q56 2458 Z1 L5 Q57 2459 Z1 L5 Q58 2460 Z1 L5 Q59 2461 Z1 L5 Q60 2462 Z1 L5 Q61 2463 Z1 L5 Q62 2464 Z1 L5 Q63 2465 Z1 L5 Q64 2466 Z1 L5 Q65 2467 Z1 L5 Q66 2468 Z1 L5 Q67 2469 Z1 L5 Q68 2470 Z1 L5 Q69 2471 Z1 L5 Q70 2472 Z1 L5 Q71 2473 Z1 L5 Q72 2474 Z1 L5 Q73 2475 Z1 L5 Q74 2476 Z1 L5 Q75 2477 Z1 L5 Q76 2478 Z1 L5 Q77 2479 Z1 L5 Q78 2480 Z1 L5 Q79 2481 Z1 L5 Q80 2482 Z1 L5 Q81 2483 Z1 L5 Q82 2484 Z1 L5 Q83 2485 Z1 L5 Q84 2486 Z1 L5 Q85 2487 Z1 L5 Q86 2488 Z1 L5 Q87 2489 Z1 L5 Q88 2490 Z1 L5 Q89 2491 Z1 L5 Q90 2492 Z1 L5 Q91 2493 Z1 L5 Q92 2494 Z1 L5 Q93 2495 Z1 L5 Q94 2496 Z1 L5 Q95 2497 Z1 L5 Q96 2498 Z1 L5 Q97 2499 Z1 L5 Q98 2500 Z1 L5 Q99 2501 Z1 L5 Q100 2502 Z1 L5 Q101 2503 Z1 L5 Q102 2504 Z1 L5 Q103 2505 Z1 L6 Q40 2506 Z1 L6 Q41 2507 Z1 L6 Q42 2508 Z1 L6 Q43 2509 Z1 L6 Q44 2510 Z1 L6 Q45 2511 Z1 L6 Q46 2512 Z1 L6 Q47 2513 Z1 L6 Q48 2514 Z1 L6 Q49 2515 Z1 L6 Q50 2516 Z1 L6 Q51 2517 Z1 L6 Q52 2518 Z1 L6 Q53 2519 Z1 L6 Q54 2520 Z1 L6 Q55 2521 Z1 L6 Q56 2522 Z1 L6 Q57 2523 Z1 L6 Q58 2524 Z1 L6 Q59 2525 Z1 L6 Q60 2526 Z1 L6 Q61 2527 Z1 L6 Q62 2528 Z1 L6 Q63 2529 Z1 L6 Q64 2530 Z1 L6 Q65 2531 Z1 L6 Q66 2532 Z1 L6 Q67 2533 Z1 L6 Q68 2534 Z1 L6 Q69 2535 Z1 L6 Q70 2536 Z1 L6 Q71 2537 Z1 L6 Q72 2538 Z1 L6 Q73 2539 Z1 L6 Q74 2540 Z1 L6 Q75 2541 Z1 L6 Q76 2542 Z1 L6 Q77 2543 Z1 L6 Q78 2544 Z1 L6 Q79 2545 Z1 L6 Q80 2546 Z1 L6 Q81 2547 Z1 L6 Q82 2548 Z1 L6 Q83 2549 Z1 L6 Q84 2550 Z1 L6 Q85 2551 Z1 L6 Q86 2552 Z1 L6 Q87 2553 Z1 L6 Q88 2554 Z1 L6 Q89 2555 Z1 L6 Q90 2556 Z1 L6 Q91 2557 Z1 L6 Q92 2558 Z1 L6 Q93 2559 Z1 L6 Q94 2560 Z1 L6 Q95 2561 Z1 L6 Q96 2562 Z1 L6 Q97 2563 Z1 L6 Q98 2564 Z1 L6 Q99 2565 Z1 L6 Q100 2566 Z1 L6 Q101 2567 Z1 L6 Q102 2568 Z1 L6 Q103 2569 Z1 L7 Q40 2570 Z1 L7 Q41 2571 Z1 L7 Q42 2572 Z1 L7 Q43 2573 Z1 L7 Q44 2574 Z1 L7 Q45 2575 Z1 L7 Q46 2576 Z1 L7 Q47 2577 Z1 L7 Q48 2578 Z1 L7 Q49 2579 Z1 L7 Q50 2580 Z1 L7 Q51 2581 Z1 L7 Q52 2582 Z1 L7 Q53 2583 Z1 L7 Q54 2584 Z1 L7 Q55 2585 Z1 L7 Q56

TABLE 1-19 2586 Z1 L7 Q57 2587 Z1 L7 Q58 2588 Z1 L7 Q59 2589 Z1 L7 Q60 2590 Z1 L7 Q61 2591 Z1 L7 Q62 2592 Z1 L7 Q63 2593 Z1 L7 Q64 2594 Z1 L7 Q65 2595 Z1 L7 Q66 2596 Z1 L7 Q67 2597 Z1 L7 Q68 2598 Z1 L7 Q69 2599 Z1 L7 Q70 2600 Z1 L7 Q71 2601 Z1 L7 Q72 2602 Z1 L7 Q73 2603 Z1 L7 Q74 2604 Z1 L7 Q75 2605 Z1 L7 Q76 2606 Z1 L7 Q77 2607 Z1 L7 Q78 2608 Z1 L7 Q79 2609 Z1 L7 Q80 2610 Z1 L7 Q81 2611 Z1 L7 Q82 2612 Z1 L7 Q83 2613 Z1 L7 Q84 2614 Z1 L7 Q85 2615 Z1 L7 Q86 2616 Z1 L7 Q87 2617 Z1 L7 Q88 2618 Z1 L7 Q89 2619 Z1 L7 Q90 2620 Z1 L7 Q91 2621 Z1 L7 Q92 2622 Z1 L7 Q93 2623 Z1 L7 Q94 2624 Z1 L7 Q95 2625 Z1 L7 Q96 2626 Z1 L7 Q97 2627 Z1 L7 Q98 2628 Z1 L7 Q99 2629 Z1 L7 Q100 2630 Z1 L7 Q101 2631 Z1 L7 Q102 2632 Z1 L7 Q103 2633 Z1 L8 Q40 2634 Z1 L8 Q41 2635 Z1 L8 Q42 2636 Z1 L8 Q43 2637 Z1 L8 Q44 2638 Z1 L8 Q45 2639 Z1 L8 Q46 2640 Z1 L8 Q47 2641 Z1 L8 Q48 2642 Z1 L8 Q49 2643 Z1 L8 Q50 2644 Z1 L8 Q51 2645 Z1 L8 Q52 2646 Z1 L8 Q53 2647 Z1 L8 Q54 2648 Z1 L8 Q55 2649 Z1 L8 Q56 2650 Z1 L8 Q57 2651 Z1 L8 Q58 2652 Z1 L8 Q59 2653 Z1 L8 Q60 2654 Z1 L8 Q64 2655 Z1 L8 Q62 2656 Z1 L8 Q63 2657 Z1 L8 Q64 2658 Z1 L8 Q65 2659 Z1 L8 Q66 2660 Z1 L8 Q67 2661 Z1 L8 Q68 2662 Z1 L8 Q69 2663 Z1 L8 Q70 2664 Z1 L8 Q71 2665 Z1 L8 Q72 2666 Z1 L8 Q73 2667 Z1 L8 Q74 2668 Z1 L8 Q75 2669 Z1 L8 Q76 2670 Z1 L8 Q77 2671 Z1 L8 Q78 2672 Z1 L8 Q79 2673 Z1 L8 Q80 2674 Z1 L8 Q81 2675 Z1 L8 Q82 2676 Z1 L8 Q83 2677 Z1 L8 Q84 2678 Z1 L8 Q85 2679 Z1 L8 Q86 2680 Z1 L8 Q87 2681 Z1 L8 Q88 2682 Z1 L8 Q89 2683 Z1 L8 Q90 2684 Z1 L8 Q91 2685 Z1 L8 Q92 2686 Z1 L8 Q93 2687 Z1 L8 Q94 2688 Z1 L8 Q95 2689 Z1 L8 Q96 2690 Z1 L8 Q97 2691 Z1 L8 Q98 2692 Z1 L8 Q99 2693 Z1 L8 Q100 2694 Z1 L8 Q101 2695 Z1 L8 Q102 2696 Z1 L8 Q103 2697 Z1 L9 Q40 2698 Z1 L9 Q41 2699 Z1 L9 Q42 2700 Z1 L9 Q43 2701 Z1 L9 Q44 2702 Z1 L9 Q45 2703 Z1 L9 Q46 2704 Z1 L9 Q47 2705 Z1 L9 Q48 2706 Z1 L9 Q49 2707 Z1 L9 Q50 2708 Z1 L9 Q51 2709 Z1 L9 Q52 2710 Z1 L9 Q53 2711 Z1 L9 Q54 2712 Z1 L9 Q55 2713 Z1 L9 Q56 2714 Z1 L9 Q57 2715 Z1 L9 Q58 2716 Z1 L9 Q59 2717 Z1 L9 Q60 2718 Z1 L9 Q61 2719 Z1 L9 Q62 2720 Z1 L9 Q63 2721 Z1 L9 Q64 2722 Z1 L9 Q65 2723 Z1 L9 Q66 2724 Z1 L9 Q67 2725 Z1 L9 Q68 2726 Z1 L9 Q69 2727 Z1 L9 Q70 2728 Z1 L9 Q71 2729 Z1 L9 Q72 2730 Z1 L9 Q73 2731 Z1 L9 Q74 2732 Z1 L9 Q75 2733 Z1 L9 Q76 2734 Z1 L9 Q77 2735 Z1 L9 Q78 2736 Z1 L9 Q79 2737 Z1 L9 Q80 2738 Z1 L9 Q81 2739 Z1 L9 Q82 2740 Z1 L9 Q83 2741 Z1 L9 Q84 2742 Z1 L9 Q85 2743 Z1 L9 Q86 2744 Z1 L9 Q87 2745 Z1 L9 Q88 2746 Z1 L9 Q89 2747 Z1 L9 Q90 2748 Z1 L9 Q91 2749 Z1 L9 Q92 2750 Z1 L9 Q93 2751 Z1 L9 Q94 2752 Z1 L9 Q95 2753 Z1 L9 Q96 2754 Z1 L9 Q97 2755 Z1 L9 Q98 2756 Z1 L9 Q99 2757 Z1 L9 Q100 2758 Z1 L9 Q101 2759 Z1 L9 Q102 2760 Z1 L9 Q103 2761 Z1 L10 Q40 2762 Z1 L10 Q41 2763 Z1 L10 Q42 2764 Z1 L10 Q43 2765 Z1 L10 Q44 2766 Z1 L10 Q45 2767 Z1 L10 Q46 2768 Z1 L10 Q47 2769 Z1 L10 Q48 2770 Z1 L10 Q49 2771 Z1 L10 Q50 2772 Z1 L10 Q51 2773 Z1 L10 Q52 2774 Z1 L10 Q53 2775 Z1 L10 Q54 2776 Z1 L10 Q55 2777 Z1 L10 Q56 2778 Z1 L10 Q57 2779 Z1 L10 Q58 2780 Z1 L10 Q59 2781 Z1 L10 Q60 2782 Z1 L10 Q61 2783 Z1 L10 Q62 2784 Z1 L10 Q63 2785 Z1 L10 Q64 2786 Z1 L10 Q65

TABLE 1-20 2787 Z1 L10 Q66 2798 Z1 L10 Q67 2789 Z1 L10 Q68 2790 Z1 L10 Q69 2791 Z1 L10 Q70 2792 Z1 L10 Q71 2793 Z1 L10 Q72 2794 Z1 L10 Q73 2795 Z1 L10 Q74 2796 Z1 L10 Q75 2797 Z1 L10 Q76 2798 Z1 L10 Q77 2799 Z1 L10 Q78 2800 Z1 L10 Q79 2801 Z1 L10 Q80 2302 Z1 L10 Q81 2803 Z1 L10 Q82 2804 Z1 L10 Q83 2805 Z1 L10 Q84 2806 Z1 L10 Q85 2807 Z1 L10 Q86 2808 Z1 L10 Q87 2809 Z1 L10 Q88 2810 Z1 L10 Q89 2811 Z1 L10 Q90 2812 Z1 L10 Q91 2813 Z1 L10 Q92 2814 Z1 L10 Q93 2815 Z1 L10 Q94 2816 Z1 L10 Q95 2817 Z1 L10 Q96 2818 Z1 L10 Q97 2819 Z1 L10 Q98 2820 Z1 L10 Q99 2821 Z1 L10 Q100 2822 Z1 L10 Q101 2823 Z1 L10 Q102 2824 Z1 L10 Q103 2825 Z1 L11 Q40 2826 Z1 L11 Q41 2827 Z1 L11 Q42 2828 Z1 L11 Q43 2829 Z1 L11 Q44 2830 Z1 L11 Q45 2831 Z1 L11 Q46 2832 Z1 L11 Q47 2833 Z1 L11 Q48 2834 Z1 L11 Q49 2835 Z1 L11 Q50 2836 Z1 L11 Q51 2837 Z1 L11 Q52 2838 Z1 L11 Q53 2839 Z1 L11 Q54 2840 Z1 L11 Q55 2841 Z1 L11 Q56 2842 Z1 L11 Q57 2843 Z1 L11 Q58 2844 Z1 L11 Q59 2845 Z1 L11 Q60 2846 Z1 L11 Q61 2847 Z1 L11 Q62 2848 Z1 L11 Q63 2849 Z1 L11 Q64 2850 Z1 L11 Q65 2851 Z1 L11 Q66 2852 Z1 L11 Q67 2853 Z1 L11 Q68 2854 Z1 L11 Q69 2855 Z1 L11 Q70 2856 Z1 L11 Q71 2857 Z1 L11 Q72 2858 Z1 L11 Q73 2859 Z1 L11 Q74 2860 Z1 L11 Q75 2861 Z1 L11 Q76 2862 Z1 L11 Q77 2863 Z1 L11 Q78 2864 Z1 L11 Q79 2865 Z1 L11 Q80 2866 Z1 L11 Q81 2867 Z1 L11 Q82 2868 Z1 L11 Q83 2869 Z1 L11 Q84 2870 Z1 L11 Q85 2871 Z1 L11 Q86 2872 Z1 L11 Q87 2873 Z1 L11 Q88 2874 Z1 L11 Q89 2875 Z1 L11 Q90 2876 Z1 L11 Q91 2877 Z1 L11 Q92 2878 Z1 L11 Q93 2879 Z1 L11 Q94 2880 Z1 L11 Q95 2881 Z1 L11 Q96 2882 Z1 L11 Q97 2883 Z1 L11 Q98 2884 Z1 L11 Q99 2885 Z1 L11 Q100 2886 Z1 L11 Q101 2887 Z1 L11 Q102 2888 Z1 L11 Q103 2889 Z1 L12 Q40 2890 Z1 L12 Q41 2891 Z1 L12 Q42 2892 Z1 L12 Q43 2893 Z1 L12 Q44 2894 Z1 L12 Q45 2895 Z1 L12 Q46 2896 Z1 L12 Q47 2897 Z1 L12 Q48 2898 Z1 L12 Q49 2899 Z1 L12 Q50 2900 Z1 L12 Q51 2901 Z1 L12 Q52 2902 Z1 L12 Q53 2903 Z1 L12 Q54 2904 Z1 L12 Q55 2905 Z1 L12 Q56 2906 Z1 L12 Q57 2907 Z1 L12 Q58 2908 Z1 L12 Q59 2909 Z1 L12 Q60 2910 Z1 L12 Q61 2911 Z1 L12 Q62 2912 Z1 L12 Q63 2913 Z1 L12 Q64 2914 Z1 L12 Q65 2915 Z1 L12 Q66 2916 Z1 L12 Q67 2917 Z1 L12 Q68 2918 Z1 L12 Q69 2919 Z1 L12 Q70 2920 Z1 L12 Q71 2921 Z1 L12 Q72 2922 Z1 L12 Q73 2923 Z1 L12 Q74 2924 Z1 L12 Q75 2925 Z1 L12 Q76 2926 Z1 L12 Q77 2927 Z1 L12 Q78 2928 Z1 L12 Q79 2929 Z1 L12 Q80 2930 Z1 L12 Q81 2931 Z1 L12 Q82 2932 Z1 L12 Q83 2933 Z1 L12 Q84 2934 Z1 L12 Q85 2935 Z1 L12 Q86 2936 Z1 L12 Q87 2937 Z1 L12 Q88 2938 Z1 L12 Q89 2939 Z1 L12 Q90 2940 Z1 L12 Q91 2941 Z1 L12 Q92 2942 Z1 L12 Q93 2943 Z1 L12 Q94 2944 Z1 L12 Q95 2945 Z1 L12 Q96 2946 Z1 L12 Q97 2947 Z1 L12 Q98 2948 Z1 L12 Q99 2949 Z1 L12 Q100 2950 Z1 L12 Q101 2951 Z1 L12 Q102 2952 Z1 L12 Q103 2953 Z1 L12 Q40 2954 Z1 L12 Q41 2955 Z1 L12 Q42 2956 Z1 L12 Q43 2957 Z1 L12 Q44 2958 Z1 L12 Q45 2959 Z1 L12 Q46 2960 Z1 L12 Q47 2961 Z1 L12 Q48 2962 Z1 L12 Q49 2963 Z1 L12 Q50 2964 Z1 L12 Q51 2965 Z1 L12 Q52 2966 Z1 L12 Q53 2967 Z1 L12 Q54 2968 Z1 L12 Q55 2969 Z1 L12 Q56 2970 Z1 L12 Q57 2971 Z1 L12 Q58 2972 Z1 L12 Q59 2973 Z1 L12 Q60 2974 Z1 L12 Q61 2975 Z1 L12 Q62 2976 Z1 L12 Q63 2977 Z1 L12 Q64 2978 Z1 L12 Q65 2979 Z1 L12 Q66 2980 Z1 L12 Q67 2981 Z1 L12 Q68 2982 Z1 L12 Q69 2983 Z1 L12 Q70 2984 Z1 L12 Q71 2985 Z1 L12 Q72 2986 Z1 L12 Q73 2987 Z1 L12 Q74

TABLE 1-21 2988 Z1 L13 Q75 2989 Z1 L13 Q76 2990 Z1 L13 Q77 2991 Z1 L13 Q78 2992 Z1 L13 Q79 2993 Z1 L13 Q80 2994 Z1 L13 Q81 2995 Z1 L13 Q82 2996 Z1 L13 Q83 2997 Z1 L13 Q84 2998 Z1 L13 Q85 2999 Z1 L13 Q86 3000 Z1 L13 Q87 3004 Z1 L13 Q88 3002 Z1 L13 Q89 3003 Z1 L13 Q90 3004 Z1 L13 Q91 3005 Z1 L13 Q92 3006 Z1 L13 Q93 3007 Z1 L13 Q94 3008 Z1 L13 Q95 3009 Z1 L13 Q96 3010 Z1 L13 Q97 3011 Z1 L13 Q98 3012 Z1 L13 Q99 3013 Z1 L13 Q100 3014 Z1 L13 Q101 3015 Z1 L13 Q102 3016 Z1 L13 Q103 3017 Z1 L14 Q40 3018 Z1 L14 Q41 3019 Z1 L14 Q42 3020 Z1 L14 Q43 3021 Z1 L14 Q44 3022 Z1 L14 Q45 3023 Z1 L14 Q46 3024 Z1 L14 Q47 3025 Z1 L14 Q48 3026 Z1 L14 Q49 3027 Z1 L14 Q50 3028 Z1 L14 Q51 3029 Z1 L14 Q52 3030 Z1 L14 Q53 3031 Z1 L14 Q54 3032 Z1 L14 Q55 3033 Z1 L14 Q56 3034 Z1 L14 Q57 3035 Z1 L14 Q58 3036 Z1 L14 Q59 3037 Z1 L14 Q60 3038 Z1 L14 Q61 3039 Z1 L14 Q62 3040 Z1 L14 Q63 3041 Z1 L14 Q64 3042 Z1 L14 Q65 3043 Z1 L14 Q66 3044 Z1 L14 Q67 3045 Z1 L14 Q68 3046 Z1 L14 Q69 3047 Z1 L14 Q70 3048 Z1 L14 Q71 3049 Z1 L14 Q72 3050 Z1 L14 Q73 3051 Z1 L14 Q74 3052 Z1 L14 Q75 3053 Z1 L14 Q76 3054 Z1 L14 Q77 3055 Z1 L14 Q78 3056 Z1 L14 Q79 3057 Z1 L14 Q80 3058 Z1 L14 Q81 3059 Z1 L14 Q82 3060 Z1 L14 Q83 3061 Z1 L14 Q84 3062 Z1 L14 Q85 3063 Z1 L14 Q86 3064 Z1 L14 Q87 3065 Z1 L14 Q88 3066 Z1 L14 Q89 3067 Z1 L14 Q90 3068 Z1 L14 Q91 3069 Z1 L14 Q92 3070 Z1 L14 Q93 3071 Z1 L14 Q94 3072 Z1 L14 Q95 3073 Z1 L14 Q96 3074 Z1 L14 Q97 3075 Z1 L14 Q98 3076 Z1 L14 Q99 3077 Z1 L14 Q100 3078 Z1 L14 Q101 3079 Z1 L14 Q102 3080 Z1 L14 Q103 3081 Z2 L1 Q40 3082 Z2 L1 Q41 3083 Z2 L1 Q42 3084 Z2 L1 Q43 3085 Z2 L1 Q44 3086 Z2 L1 Q45 3087 Z2 L1 Q46 3088 Z2 L1 Q47 3089 Z2 L1 Q48 3090 Z2 L1 Q49 3091 Z2 L1 Q50 3092 Z2 L1 Q51 3093 Z2 L1 Q52 3094 Z2 L1 Q53 3095 Z2 L1 Q54 3096 Z2 L1 Q55 3097 Z2 L1 Q56 3098 Z2 L1 Q57 3099 Z2 L1 Q58 3100 Z2 L1 Q59 3101 Z2 L1 Q60 3102 Z2 L1 Q61 3103 Z2 L1 Q62 3104 Z2 L1 Q63 3105 Z2 L1 Q64 3106 Z2 L1 Q65 3107 Z2 L1 Q66 3108 Z2 L1 Q67 3109 Z2 L1 Q68 3110 Z2 L1 Q69 3111 Z2 L1 Q70 3112 Z2 L1 Q71 3113 Z2 L1 Q72 3114 Z2 L1 Q63 3115 Z2 L1 Q74 3116 Z2 L1 Q75 3117 Z2 L1 Q73 3118 Z2 L1 Q74 3119 Z2 L1 Q75 3120 Z2 L1 Q76 3121 Z2 L1 Q77 3122 Z2 L1 Q81 3123 Z2 L1 Q82 3124 Z2 L1 Q83 3125 Z2 L1 Q84 3126 Z2 L1 Q85 3127 Z2 L1 Q86 3128 Z2 L1 Q87 3129 Z2 L1 Q88 3130 Z2 L1 Q89 3131 Z2 L1 Q90 3132 Z2 L1 Q91 3133 Z2 L1 Q92 3134 Z2 L1 Q93 3135 Z2 L1 Q94 3136 Z2 L1 Q95 3137 Z2 L1 Q96 3138 Z2 L1 Q97 3139 Z2 L1 Q98 3140 Z2 L1 Q99 3141 Z2 L1 Q100 3142 Z2 L1 Q101 3143 Z2 L1 Q102 3144 Z2 L1 Q103 3145 Z2 L1 Q40 3146 Z2 L1 Q41 3147 Z2 L1 Q42 3148 Z2 L1 Q43 3149 Z2 L1 Q44 3150 Z2 L1 Q45 3151 Z2 L1 Q46 3152 Z2 L1 Q47 3153 Z2 L1 Q48 3154 Z2 L1 Q49 3155 Z2 L1 Q50 3156 Z2 L1 Q51 3157 Z2 L1 Q52 3158 Z2 L1 Q53 3159 Z2 L1 Q54 3160 Z2 L1 Q55 3161 Z2 L1 Q56 3162 Z2 L1 Q57 3163 Z2 L1 Q58 3164 Z2 L1 Q59 3165 Z2 L1 Q60 3166 Z2 L1 Q61 3167 Z2 L1 Q62 3168 Z2 L1 Q63 3169 Z2 L1 Q64 3170 Z2 L1 Q65 6171 Z2 L1 Q66 6172 Z2 L1 Q667 6173 Z2 L1 Q68 6164 Z2 L1 Q69 6165 Z2 L1 Q70 6166 Z2 L1 Q71 6167 Z2 L1 Q72 6168 Z2 L1 Q73 6169 Z2 L1 Q74 6170 Z2 L1 Q75 6171 Z2 L1 Q76 6172 Z2 L1 Q77 6173 Z2 L1 Q78 6174 Z2 L1 Q79 6175 Z2 L1 Q80 6176 Z2 L1 Q81 6177 Z2 L1 Q82 6178 Z2 L1 Q83

TABLE 1-22 3189 Z2 L2 Q84 3190 Z2 L2 Q85 3191 Z2 L2 Q86 3192 Z2 L2 Q87 3193 Z2 L2 Q88 3194 Z2 L2 Q89 3195 Z2 L2 Q90 3196 Z2 L2 Q91 3197 Z2 L2 Q92 3198 Z2 L2 Q93 3199 Z2 L2 Q94 3200 Z2 L2 Q95 3201 Z2 L2 Q96 3202 Z2 L2 Q97 3203 Z2 L2 Q98 3204 Z2 L2 Q99 3205 Z2 L2 Q100 3206 Z2 L2 Q101 3207 Z2 L2 Q102 3208 Z2 L2 Q103 3209 Z2 L3 Q40 3210 Z2 L3 Q41 3211 Z2 L3 Q42 3212 Z2 L3 Q43 3213 Z2 L3 Q44 3214 Z2 L3 Q45 3215 Z2 L3 Q46 3216 Z2 L3 Q47 3217 Z2 L3 Q48 3218 Z2 L3 Q49 3219 Z2 L3 Q50 3220 Z2 L3 Q51 3221 Z2 L3 Q52 3222 Z2 L3 Q53 3223 Z2 L3 Q54 3224 Z2 L3 Q55 3225 Z2 L3 Q56 3226 Z2 L3 Q57 3227 Z2 L3 Q58 3228 Z2 L3 Q59 3229 Z2 L3 Q60 3230 Z2 L3 Q61 3231 Z2 L3 Q62 3232 Z2 L3 Q63 3233 Z2 L3 Q64 3234 Z2 L3 Q65 3235 Z2 L3 Q66 3236 Z2 L3 Q67 3237 Z2 L3 Q68 3238 Z2 L3 Q69 3239 Z2 L3 Q70 3240 Z2 L3 Q71 3241 Z2 L3 Q72 3242 Z2 L3 Q73 3243 Z2 L3 Q74 3244 Z2 L3 Q75 3245 Z2 L3 Q76 3246 Z2 L3 Q77 3247 Z2 L3 Q78 3248 Z2 L3 Q79 3249 Z2 L3 Q80 3250 Z2 L3 Q81 3251 Z2 L3 Q82 3252 Z2 L3 Q83 3253 Z2 L3 Q84 3254 Z2 L3 Q85 3255 Z2 L3 Q86 3256 Z2 L3 Q87 3257 Z2 L3 Q83 3258 Z2 L3 Q89 3259 Z2 L3 Q90 3260 Z2 L3 Q91 3261 Z2 L3 Q92 3262 Z2 L3 Q93 3263 Z2 L3 Q94 3264 Z2 L3 Q95 3265 Z2 L3 Q96 3266 Z2 L3 Q97 3267 Z2 L3 Q98 3268 Z2 L3 Q99 3269 Z2 L3 Q100 3270 Z2 L3 Q101 3271 Z2 L3 Q102 3272 Z2 L3 Q103 3273 Z2 L4 Q40 3274 Z2 L4 Q41 3275 Z2 L4 Q42 3276 Z2 L4 Q43 3277 Z2 L4 Q44 3278 Z2 L4 Q45 3279 Z2 L4 Q46 3280 Z2 L4 Q47 3281 Z2 L4 Q48 3282 Z2 L4 Q49 3283 Z2 L4 Q50 3284 Z2 L4 Q51 3285 Z2 L4 Q52 3286 Z2 L4 Q53 3287 Z2 L4 Q54 3288 Z2 L4 Q55 3289 Z2 L4 Q56 3290 Z2 L4 Q57 3291 Z2 L4 Q58 3292 Z2 L4 Q59 3293 Z2 L4 Q60 3294 Z2 L4 Q61 3295 Z2 L4 Q62 3296 Z2 L4 Q63 3297 Z2 L4 Q64 3298 Z2 L4 Q65 3299 Z2 L4 Q66 3301 Z2 L4 Q67 3302 Z2 L4 Q68 3303 Z2 L4 Q69 3304 Z2 L4 Q70 3305 Z2 L4 Q71 3306 Z2 L4 Q72 3307 Z2 L4 Q73 3308 Z2 L4 Q74 3309 Z2 L4 Q75 3310 Z2 L4 Q76 3311 Z2 L4 Q77 3312 Z2 L4 Q78 3313 Z2 L4 Q79 3314 Z2 L4 Q80 3315 Z2 L4 Q81 3316 Z2 L4 Q82 3317 Z2 L4 Q83 3318 Z2 L4 Q84 3319 Z2 L4 Q85 3320 Z2 L4 Q86 3321 Z2 L4 Q87 3322 Z2 L4 Q88 3323 Z2 L4 Q89 3323 Z2 L4 Q90 3324 Z2 L4 Q91 3325 Z2 L4 Q92 3326 Z2 L4 Q93 3327 Z2 L4 Q94 3328 Z2 L4 Q95 3329 Z2 L4 Q96 3330 Z2 L4 Q97 3331 Z2 L4 Q98 3332 Z2 L4 Q99 3333 Z2 L4 Q100 3334 Z2 L4 Q101 3335 Z2 L4 Q102 3336 Z2 L4 Q103 3337 Z2 L5 Q40 3338 Z2 L5 Q41 3339 Z2 L5 Q42 3340 Z2 L5 Q43 3341 Z2 L5 Q44 3342 Z2 L5 Q45 3343 Z2 L5 Q46 3344 Z2 L5 Q47 3345 Z2 L5 Q48 3346 Z2 L5 Q49 3347 Z2 L5 Q50 3348 Z2 L5 Q51 3349 Z2 L5 Q52 3350 Z2 L5 Q53 3351 Z2 L5 Q54 3352 Z2 L5 Q55 3353 Z2 L5 Q56 3354 Z2 L5 Q57 3355 Z2 L5 Q58 3356 Z2 L5 Q59 3357 Z2 L5 Q60 3358 Z2 L5 Q61 3359 Z2 L5 Q62 3360 Z2 L5 Q63 3361 Z2 L5 Q64 3362 Z2 L5 Q65 3363 Z2 L5 Q66 3364 Z2 L5 Q67 3365 Z2 L5 Q68 3366 Z2 L5 Q69 3367 Z2 L5 Q70 3368 Z2 L5 Q71 3369 Z2 L5 Q72 3370 Z2 L5 Q73 3371 Z2 L5 Q74 3372 Z2 L5 Q75 3373 Z2 L5 Q76 3374 Z2 L5 Q77 3375 Z2 L5 Q78 3376 Z2 L5 Q79 3377 Z2 L5 Q80 3378 Z2 L5 Q81 3379 Z2 L5 Q82 3380 Z2 L5 Q83 3381 Z2 L5 Q84 3382 Z2 L5 Q85 3383 Z2 L5 Q86 3384 Z2 L5 Q87 3385 Z2 L5 Q88 3386 Z2 L5 Q89 3387 Z2 L5 Q90 3388 Z2 L5 Q91 3389 Z2 L5 Q92

TABLE 1-23 3390 Z2 L5 Q93 3391 Z2 L5 Q94 3392 Z2 L5 Q95 3393 Z2 L5 Q96 3394 Z2 L5 Q97 3395 Z2 L5 Q98 3396 Z2 L5 Q99 3397 Z2 L5 Q100 3398 Z2 L5 Q101 3399 Z2 L5 Q102 3400 Z2 L5 Q103 3401 Z2 L6 Q40 3402 Z2 L6 Q41 3403 Z2 L6 Q42 3404 Z2 L6 Q43 3405 Z2 L6 Q44 3406 Z2 L6 Q45 3407 Z2 L6 Q46 3408 Z2 L6 Q47 3409 Z2 L6 Q48 3410 Z2 L6 Q49 3411 Z2 L6 Q50 3412 Z2 L6 Q51 3413 Z2 L6 Q52 3414 Z2 L6 Q53 3415 Z2 L6 Q54 3416 Z2 L6 Q55 3417 Z2 L6 Q56 3418 Z2 L6 Q57 3419 Z2 L6 Q58 3420 Z2 L6 Q59 3421 Z2 L6 Q60 3422 Z2 L6 Q61 3423 Z2 L6 Q62 3424 Z2 L6 Q63 3425 Z2 L6 Q64 3426 Z2 L6 Q65 3427 Z2 L6 Q66 3428 Z2 L6 Q67 3429 Z2 L6 Q68 3430 Z2 L6 Q69 3431 Z2 L6 Q70 3432 Z2 L6 Q71 3433 Z2 L6 Q72 3434 Z2 L6 Q73 3435 Z2 L6 Q74 3436 Z2 L6 Q75 3437 Z2 L6 Q76 3438 Z2 L6 Q77 3439 Z2 L6 Q78 3440 Z2 L6 Q79 3441 Z2 L6 Q80 3442 Z2 L6 Q81 3443 Z2 L6 Q82 3444 Z2 L6 Q83 3445 Z2 L6 Q84 3446 Z2 L6 Q85 3447 Z2 L6 Q86 3448 Z2 L6 Q87 3449 Z2 L6 Q88 3450 Z2 L6 Q89 3451 Z2 L6 Q90 3452 Z2 L6 Q91 3453 Z2 L6 Q92 3454 Z2 L6 Q93 3455 Z2 L6 Q94 3456 Z2 L6 Q95 3457 Z2 L6 Q96 3458 Z2 L6 Q97 3459 Z2 L6 Q98 3460 Z2 L6 Q99 3461 Z2 L6 Q100 3462 Z2 L6 Q101 3463 Z2 L6 Q102 3464 Z2 L6 Q103 3465 Z2 L7 Q40 3466 Z2 L7 Q41 3467 Z2 L7 Q42 3468 Z2 L7 Q43 3469 Z2 L7 Q44 3470 Z2 L7 Q45 3471 Z2 L7 Q46 3472 Z2 L7 Q47 3473 Z2 L7 Q48 3474 Z2 L7 Q49 3475 Z2 L7 Q50 3476 Z2 L7 Q51 3477 Z2 L7 Q52 3478 Z2 L7 Q53 3479 Z2 L7 Q54 3480 Z2 L7 Q55 3481 Z2 L7 Q56 3482 Z2 L7 Q57 3483 Z2 L7 Q58 3484 Z2 L7 Q59 3485 Z2 L7 Q60 3486 Z2 L7 Q61 3487 Z2 L7 Q62 3488 Z2 L7 Q63 3489 Z2 L7 Q64 3490 Z2 L7 Q65 3491 Z2 L7 Q66 3492 Z2 L7 Q67 3493 Z2 L7 Q68 3494 Z2 L7 Q69 3495 Z2 L7 Q70 3496 Z2 L7 Q71 3497 Z2 L7 Q72 3498 Z2 L7 Q73 3499 Z2 L7 Q74 3500 Z2 L7 Q75 3501 Z2 L7 Q76 3502 Z2 L7 Q77 3503 Z2 L7 Q78 3504 Z2 L7 Q79 3505 Z2 L7 Q80 3506 Z2 L7 Q81 3507 Z2 L7 Q82 3508 Z2 L7 Q83 3509 Z2 L7 Q84 3510 Z2 L7 Q85 3511 Z2 L7 Q86 3512 Z2 L7 Q87 3513 Z2 L7 Q88 3514 Z2 L7 Q89 3515 Z2 L7 Q90 3516 Z2 L7 Q91 3517 Z2 L7 Q92 3518 Z2 L7 Q93 3519 Z2 L7 Q94 3520 Z2 L7 Q95 3521 Z2 L7 Q96 3522 Z2 L7 Q97 3523 Z2 L7 Q98 3524 Z2 L7 Q99 3525 Z2 L7 Q100 3526 Z2 L7 Q101 3527 Z2 L7 Q102 3528 Z2 L7 Q103 3529 Z2 L8 Q40 3530 Z2 L8 Q41 3531 Z2 L8 Q42 3532 Z2 L8 Q43 3533 Z2 L8 Q44 3534 Z2 L8 Q45 3535 Z2 L8 Q46 3536 Z2 L8 Q47 3537 Z2 L8 Q48 3538 Z2 L8 Q49 3539 Z2 L8 Q50 3540 Z2 L8 Q51 3541 Z2 L8 Q52 3542 Z2 L8 Q53 3543 Z2 L8 Q54 3544 Z2 L8 Q55 3545 Z2 L8 Q56 3546 Z2 L8 Q57 3547 Z2 L8 Q58 3548 Z2 L8 Q59 3549 Z2 L8 Q60 3550 Z2 L8 Q61 3551 Z2 L8 Q62 3552 Z2 L8 Q63 3553 Z2 L8 Q64 3554 Z2 L8 Q65 3555 Z2 L8 Q66 3556 Z2 L8 Q67 3557 Z2 L8 Q68 3558 Z2 L8 Q69 3559 Z2 L8 Q70 3560 Z2 L8 Q71 3561 Z2 L8 Q72 3562 Z2 L8 Q73 3563 Z2 L8 Q74 3564 Z2 L8 Q75 3565 Z2 L8 Q76 3566 Z2 L8 Q77 3567 Z2 L8 Q78 3568 Z2 L8 Q79 3569 Z2 L8 Q80 3570 Z2 L8 Q81 3571 Z2 L8 Q82 3572 Z2 L8 Q83 3573 Z2 L8 Q84 3574 Z2 L8 Q85 3575 Z2 L8 Q86 3576 Z2 L8 Q87 3577 Z2 L8 Q88 3578 Z2 L8 Q89 3579 Z2 L8 Q90 3580 Z2 L8 Q91 3581 Z2 L8 Q92 3582 Z2 L8 Q93 3583 Z2 L8 Q94 3584 Z2 L8 Q95 3585 Z2 L8 Q96 3586 Z2 L8 Q97 3587 Z2 L8 Q98 3588 Z2 L8 Q99 3589 Z2 L8 Q100 3590 Z2 L8 Q101

TABLE 1-24 3591 Z2 L8 Q102 3592 Z2 L8 Q103 3593 Z2 L9 Q40 3594 Z2 L9 Q41 3595 Z2 L9 Q42 3596 Z2 L9 Q43 3597 Z2 L9 Q44 3598 Z2 L9 Q45 3599 Z2 L9 Q45 3600 Z2 L9 Q47 3601 Z2 L9 Q48 3602 Z2 L9 Q49 3603 Z2 L9 Q50 3604 Z2 L9 Q51 3605 Z2 L9 Q52 3606 Z2 L9 Q53 3607 Z2 L9 Q54 3608 Z2 L9 Q55 3609 Z2 L9 Q55 3610 Z2 L9 Q57 3611 Z2 L9 Q58 3612 Z2 L9 Q59 3613 Z2 L9 Q60 3614 Z2 L9 Q61 3615 Z2 L9 Q62 3616 Z2 L9 Q63 3617 Z2 L9 Q64 3618 Z2 L9 Q65 3619 Z2 L9 Q66 3620 Z2 L9 Q67 3621 Z2 L9 Q68 3622 Z2 L9 Q69 3623 Z2 L9 Q70 3624 Z2 L9 Q71 3625 Z2 L9 Q72 3626 Z2 L9 Q73 3627 Z2 L9 Q74 3628 Z2 L9 Q75 3629 Z2 L9 Q76 3630 Z2 L9 Q77 3631 Z2 L9 Q78 3632 Z2 L9 Q79 3633 Z2 L9 Q80 3634 Z2 L9 Q81 3635 Z2 L9 Q82 3636 Z2 L9 Q83 3637 Z2 L9 Q84 3638 Z2 L9 Q85 3639 Z2 L9 Q86 3640 Z2 L9 Q87 3641 Z2 L9 Q88 3642 Z2 L9 Q89 3643 Z2 L9 Q90 3644 Z2 L9 Q91 3645 Z2 L9 Q92 3646 Z2 L9 Q93 3647 Z2 L9 Q94 3648 Z2 L9 Q95 3649 Z2 L9 Q96 3650 Z2 L9 Q97 3651 Z2 L9 Q98 3652 Z2 L9 Q99 3653 Z2 L9 Q100 3654 Z2 L9 Q101 3655 Z2 L9 Q102 3656 Z2 L9 Q103 3657 Z2 L10 Q40 3658 Z2 L10 Q41 3659 Z2 L10 Q42 3660 Z2 L10 Q43 3661 Z2 L10 Q44 3662 Z2 L10 Q45 3663 Z2 L10 Q46 3664 Z2 L10 Q47 3665 Z2 L10 Q48 3666 Z2 L10 Q49 3667 Z2 L10 Q50 3668 Z2 L10 Q51 3669 Z2 L10 Q52 3670 Z2 L10 Q53 3671 Z2 L10 Q54 3672 Z2 L10 Q55 3673 Z2 L10 Q56 3674 Z2 L10 Q57 3675 Z2 L10 Q58 3676 Z2 L10 Q59 3677 Z2 L10 Q50 3678 Z2 L10 Q61 3679 Z2 L10 Q62 3680 Z2 L10 Q63 3681 Z2 L10 Q64 3682 Z2 L10 Q65 3683 Z2 L10 Q56 3684 Z2 L10 Q57 3685 Z2 L10 Q58 3686 Z2 L10 Q69 3687 Z2 L10 Q70 3688 Z2 L10 Q71 3689 Z2 L10 Q72 3690 Z2 L10 Q73 3691 Z2 L10 Q74 3692 Z2 L10 Q75 3693 Z2 L10 Q76 3694 Z2 L10 Q77 3695 Z2 L10 Q78 3696 Z2 L10 Q79 3697 Z2 L10 Q80 3698 Z2 L10 Q81 3699 Z2 L10 Q82 3700 Z2 L10 Q83 3701 Z2 L10 Q84 3702 Z2 L10 Q85 3703 Z2 L10 Q86 3704 Z2 L10 Q87 3705 Z2 L10 Q88 3706 Z2 L10 Q89 3707 Z2 L10 Q90 3708 Z2 L10 Q91 3709 Z2 L10 Q92 3710 Z2 L10 Q93 3711 Z2 L10 Q94 3712 Z2 L10 Q95 3713 Z2 L10 Q96 3714 Z2 L10 Q97 3715 Z2 L10 Q98 3716 Z2 L10 Q99 3717 Z2 L10 Q100 3718 Z2 L10 Q101 3719 Z2 L10 Q102 3720 Z2 L10 Q103 3721 Z2 L10 Q40 3722 Z2 L10 Q41 3723 Z2 L10 Q42 3724 Z2 L10 Q43 3725 Z2 L11 Q44 3726 Z2 L11 Q45 3727 Z2 L11 Q46 3728 Z2 L11 Q47 3729 Z2 L11 Q48 3730 Z2 L11 Q49 3731 Z2 L11 Q50 3732 Z2 L11 Q51 3733 Z2 L11 Q52 3734 Z2 L11 Q53 3735 Z2 L11 Q54 3736 Z2 L11 Q55 3737 Z2 L11 Q55 3738 Z2 L11 Q57 3739 Z2 L11 Q58 3740 Z2 L11 Q59 3741 Z2 L11 Q60 3742 Z2 L11 Q61 3743 Z2 L11 Q62 3744 Z2 L11 Q63 3745 Z2 L11 Q64 3746 Z2 L11 Q65 3747 Z2 L11 Q66 3748 Z2 L11 Q67 3749 Z2 L11 Q68 3750 Z2 L11 Q69 3751 Z2 L11 Q70 3752 Z2 L11 Q71 3753 Z2 L11 Q72 3754 Z2 L11 Q73 3755 Z2 L11 Q74 3756 Z2 L11 Q75 3757 Z2 L11 Q76 3758 Z2 L11 Q77 3759 Z2 L11 Q78 3760 Z2 L11 Q79 3761 Z2 L11 Q80 3762 Z2 L11 Q81 3763 Z2 L11 Q82 3764 Z2 L11 Q83 3765 Z2 L11 Q84 3766 Z2 L11 Q85 3767 Z2 L11 Q86 3768 Z2 L11 Q87 3769 Z2 L11 Q88 3770 Z2 L11 Q89 3771 Z2 L11 Q90 3772 Z2 L11 Q91 3773 Z2 L11 Q92 3774 Z2 L11 Q93 3775 Z2 L11 Q94 3776 Z2 L11 Q95 3777 Z2 L11 Q96 3778 Z2 L11 Q97 3779 Z2 L11 Q98 3780 Z2 L11 Q99 3781 Z2 L11 Q100 3782 Z2 L11 Q101 3773 Z2 L11 Q102 3774 Z2 L11 Q103 3775 Z2 L11 Q40 3786 Z2 L11 Q41 3787 Z2 L11 Q42 3788 Z2 L11 Q43 3789 Z2 L11 Q44 3790 Z2 L11 Q45 3791 Z2 L11 Q46

TABLE 1-25 3792 Z2 L12 Q47 3793 Z2 L12 Q48 3794 Z2 L12 Q49 3795 Z2 L12 Q50 3796 Z2 L12 Q51 3797 Z2 L12 Q52 3798 Z2 L12 Q53 3799 Z2 L12 Q54 3800 Z2 L12 Q55 3801 Z2 L12 Q56 3802 Z2 L12 Q57 3803 Z2 L12 Q58 3804 Z2 L12 Q59 3805 Z2 L12 Q60 3806 Z2 L12 Q61 3807 Z2 L12 Q62 3808 Z2 L12 Q63 3809 Z2 L12 Q64 3810 Z2 L12 Q65 3811 Z2 L12 Q66 3812 Z2 L12 Q67 3813 Z2 L12 Q68 3814 Z2 L12 Q69 3815 Z2 L12 Q70 3816 Z2 L12 Q71 3817 Z2 L12 Q72 3818 Z2 L12 Q73 3819 Z2 L12 Q74 3820 Z2 L12 Q75 3821 Z2 L12 Q76 3822 Z2 L12 Q77 3823 Z2 L12 Q78 3824 Z2 L12 Q79 3825 Z2 L12 Q80 3826 Z2 L12 Q81 3827 Z2 L12 Q82 3828 Z2 L12 Q83 3829 Z2 L12 Q84 3830 Z2 L12 Q85 3831 Z2 L12 Q86 3832 Z2 L12 Q87 3833 Z2 L12 Q88 3834 Z2 L12 Q89 3835 Z2 L12 Q90 3836 Z2 L12 Q91 3837 Z2 L12 Q92 3838 Z2 L12 Q93 3839 Z2 L12 Q94 3840 Z2 L12 Q95 3841 Z2 L12 Q96 3842 Z2 L12 Q97 3843 Z2 L12 Q98 3844 Z2 L12 Q99 3845 Z2 L12 Q100 3846 Z2 L12 Q101 3847 Z2 L12 Q102 3848 Z2 L12 Q103 3849 Z2 L12 Q40 3850 Z2 L12 Q41 3851 Z2 L12 Q42 3852 Z2 L12 Q43 3853 Z2 L12 Q44 3854 Z2 L12 Q45 3855 Z2 L12 Q46 3856 Z2 L12 Q47 3857 Z2 L12 Q48 3858 Z2 L12 Q49 3859 Z2 L13 Q50 3860 Z2 L13 Q51 3861 Z2 L13 Q52 3862 Z2 L13 Q53 3863 Z2 L13 Q54 3864 Z2 L13 Q55 3865 Z2 L13 Q56 3866 Z2 L13 Q57 3867 Z2 L13 Q53 3868 Z2 L13 Q59 3869 Z2 L13 Q60 3870 Z2 L13 Q61 3871 Z2 L13 Q62 3872 Z2 L13 Q63 3873 Z2 L13 Q64 3874 Z2 L13 Q65 3875 72 L13 Q66 3876 Z2 L13 Q67 3877 Z2 L13 Q68 3878 Z2 L13 Q69 3879 Z2 L13 Q70 3880 Z2 L13 Q71 3881 Z2 L13 Q72 3882 Z2 L13 Q73 3883 Z2 L13 Q74 3884 Z2 L13 Q75 3885 Z2 L13 Q76 3886 Z2 L13 Q77 3887 Z2 L13 Q78 3888 Z2 L13 Q79 3889 Z2 L13 Q80 3890 Z2 L13 Q81 3891 Z2 L13 Q82 3892 Z2 L13 Q83 3893 Z2 L13 Q34 3894 Z2 L13 Q85 3895 Z2 L13 Q86 3896 Z2 L13 Q87 3897 Z2 L13 Q88 3898 Z2 L13 Q89 3899 Z2 L13 Q90 3900 Z2 L13 Q91 3901 Z2 L13 Q92 3902 Z2 L13 Q93 3903 Z2 L13 Q94 3904 Z2 L13 Q95 3905 Z2 L13 Q96 3906 Z2 L13 Q97 3907 Z2 L13 Q98 3908 Z2 L13 Q99 3909 Z2 L13 Q100 3910 Z2 L13 Q102 3911 Z2 L13 Q103 3912 Z2 L14 Q40 3913 Z2 L14 Q41 3914 Z2 L14 Q42 3915 Z2 L14 Q43 3916 Z2 L14 Q44 3917 Z2 L14 Q45 3918 Z2 L14 Q46 3919 Z2 L14 Q47 3920 Z2 L14 Q48 3921 Z2 L14 Q49 3922 Z2 L14 Q50 3923 Z2 L14 Q51 3924 Z2 L14 Q52 3925 Z2 L14 Q53 3926 Z2 L14 Q53 3927 Z2 L14 Q54 3928 Z2 L14 Q55 3929 Z2 L14 Q56 3930 Z2 L14 Q57 3931 Z2 L14 Q58 3932 Z2 L14 Q59 3933 Z2 L14 Q60 3934 Z2 L14 Q61 3935 Z2 L14 Q62 3936 Z2 L14 Q63 3937 Z2 L14 Q64 3938 Z2 L14 Q65 3939 Z2 L14 Q66 3940 Z2 L14 Q67 3941 Z2 L14 Q68 3942 Z2 L14 Q69 3943 Z2 L14 Q70 3944 Z2 L14 Q71 3945 Z2 L14 Q72 3946 Z2 L14 Q73 3947 Z2 L14 Q74 3948 Z2 L14 Q75 3949 Z2 L14 Q76 3950 Z2 L14 Q77 3951 Z2 L14 Q78 3952 Z2 L14 Q79 3953 Z2 L14 Q80 3954 Z2 L14 Q81 3955 Z2 L14 Q82 3956 Z2 L14 Q83 3957 Z2 L14 Q84 3958 Z2 L14 Q85 3959 Z2 L14 Q86 3960 Z2 L14 Q87 3961 Z2 L14 Q88 3962 Z2 L14 Q89 3963 Z2 L14 Q90 3964 Z2 L14 Q91 3965 Z2 L14 Q92 3966 Z2 L14 Q93 3967 Z2 L14 Q94 3968 Z2 L14 Q95 3969 Z2 L14 Q96 3970 Z2 L14 Q97 3971 Z2 L14 Q98 3972 Z2 L14 Q99 3973 Z2 L14 Q100 3974 Z2 L14 Q101 3975 Z2 L14 Q102 3976 Z2 L14 Q103 3977 Z2 L1 Q40 3978 Z2 L1 Q41 3979 Z2 L1 Q42 3980 Z2 L1 Q43 3981 Z2 L1 Q44 3982 Z2 L1 Q45 3983 Z2 L1 Q46 3984 Z2 L1 Q47 3985 Z2 L1 Q48 3986 Z2 L1 Q49 3987 Z2 L1 Q50 3988 Z2 L1 Q51 3989 Z2 L1 Q52 3990 Z2 L1 Q53 3991 Z2 L1 Q54 3992 Z2 L1 Q55

TABLE 1-26 3993 Z3 L1 Q56 3994 Z3 L1 Q57 3995 Z3 L1 Q58 3996 Z3 L1 Q59 3997 Z3 L1 Q60 3998 Z3 L1 Q61 3999 Z3 L1 Q62 4000 Z3 L1 Q63 4001 Z3 L1 Q64 4002 Z3 L1 Q65 4003 Z3 L1 Q66 4004 Z3 L1 Q67 4005 Z3 L1 Q68 4006 Z3 L1 Q69 4007 Z3 L1 Q70 4008 Z3 L1 Q71 4009 Z3 L1 Q72 4010 Z3 L1 Q73 4011 Z3 L1 Q74 4012 Z3 L1 Q75 4013 Z3 L1 Q75 4014 Z3 L1 Q77 4015 Z3 L1 Q78 4016 Z3 L1 Q79 4017 Z3 L1 Q80 4018 Z3 L1 Q81 4019 Z3 L1 Q82 4020 Z3 L1 Q83 4021 Z3 L1 Q84 4022 Z3 L1 Q85 4023 Z3 L1 Q86 4024 Z3 L1 Q87 4025 Z3 L1 Q88 4026 Z3 L1 Q89 4027 Z3 L1 Q90 4028 Z3 L1 Q91 4029 Z3 L1 Q92 4030 Z3 L1 Q93 4031 Z3 L1 Q94 4032 Z3 L1 Q95 4033 Z3 L1 Q96 4034 Z3 L1 Q97 4035 Z3 L1 Q98 4036 Z3 L1 Q99 4037 Z3 L1 Q100 4038 Z3 L1 Q101 4039 Z3 L1 Q102 4040 Z3 L1 Q103 4041 Z3 L1 Q40 4042 Z3 L1 Q41 4043 Z3 L1 Q42 4044 Z3 L1 Q43 4045 Z3 L1 Q44 4046 Z3 L1 Q45 4047 Z3 L1 Q46 4048 Z3 L1 Q47 4049 Z3 L1 Q48 4050 Z3 L1 Q49 4051 Z3 L1 Q50 4052 Z3 L1 Q51 4053 Z3 L1 Q52 4054 Z3 L1 Q53 4055 Z3 L1 Q54 4056 Z3 L1 Q55 4057 Z3 L1 Q56 4058 Z3 L1 Q57 4059 Z3 L1 Q58 4060 Z3 L2 Q59 4061 Z3 L2 Q60 4062 Z3 L2 Q61 4063 Z3 L2 Q62 4064 Z3 L2 Q63 4065 Z3 L2 Q64 4066 Z3 L2 Q65 4067 Z3 L2 Q66 4068 Z3 L2 Q67 4069 Z3 L2 Q68 4070 Z3 L2 Q69 4071 Z3 L2 Q70 4072 Z3 L2 Q71 4073 Z3 L2 Q72 4074 Z3 L2 Q73 4075 Z3 L2 Q74 4076 Z3 L2 Q75 4077 Z3 L2 Q76 4078 Z3 L2 Q77 4079 Z3 L2 Q78 4080 Z3 L2 Q79 4081 Z3 L2 Q80 4082 Z3 L2 Q81 4083 Z3 L2 Q82 4084 Z3 L2 Q83 4085 Z3 L2 Q84 4086 Z3 L2 Q85 4087 Z3 L2 Q86 4088 Z3 L2 Q87 4089 Z3 L2 Q88 4090 Z3 L2 Q89 4091 Z3 L2 Q90 4092 Z3 L2 Q91 4093 Z3 L2 Q92 4094 Z3 L2 Q93 4095 Z3 L2 Q94 4096 Z3 L2 Q95 4097 Z3 L2 Q96 4098 Z3 L2 Q97 4099 Z3 L2 Q98 4100 Z3 L2 Q99 4101 Z3 L2 Q100 4102 Z3 L2 Q101 4103 Z3 L2 Q102 4104 Z3 L2 Q103 4105 Z3 L3 Q40 4106 Z3 L3 Q41 4107 Z3 L3 Q42 4108 Z3 L3 Q43 4109 Z3 L3 Q44 4110 Z3 L3 Q45 4111 Z3 L3 Q46 4112 Z3 L3 Q47 4113 Z3 L3 Q48 4114 Z3 L3 Q49 4115 Z3 L3 Q50 4116 Z3 L3 Q51 4117 Z3 L3 Q52 4118 Z3 L3 Q53 4119 Z3 L3 Q54 4120 Z3 L3 Q55 4121 Z3 L3 Q56 4122 Z3 L3 Q57 4123 Z3 L3 Q58 4126 Z3 L3 Q59 4125 Z3 L3 Q60 4126 Z3 L3 Q61 4127 Z3 L3 Q62 4128 Z3 L3 Q63 4129 Z3 L3 Q64 4130 Z3 L3 Q65 4131 Z3 L3 Q66 4132 Z3 L3 Q67 4133 Z3 L3 Q68 4134 Z3 L3 Q69 4135 Z3 L3 Q70 4136 Z3 L3 Q71 4137 Z3 L3 Q72 4138 Z3 L3 Q73 4139 Z3 L3 Q74 4140 Z3 L3 Q75 4141 Z3 L3 Q76 4142 Z3 L3 Q77 4143 Z3 L3 Q78 4144 Z3 L3 Q79 4145 Z3 L3 Q80 4146 Z3 L3 Q81 4147 Z3 L3 Q82 4148 Z3 L3 Q83 4149 Z3 L3 Q84 4150 Z3 L3 Q85 4151 Z3 L3 Q86 4152 Z3 L3 Q87 4153 Z3 L3 Q88 4154 Z3 L3 Q89 4155 Z3 L3 Q90 4156 Z3 L3 Q91 4157 Z3 L3 Q92 4158 Z3 L3 Q93 4159 Z3 L3 Q94 4160 Z3 L3 Q95 4461 Z3 L3 Q96 4162 Z3 L3 Q97 4163 Z3 L3 Q98 4164 Z3 L3 Q99 4165 Z3 L3 Q100 4166 Z3 L3 Q101 4167 Z3 L3 Q102 4168 Z3 L3 Q103 4169 Z3 L4 Q40 4170 Z3 L4 Q41 4171 Z3 L4 Q42 4172 Z3 L4 Q43 4173 Z3 L4 Q44 4174 Z3 L4 Q45 4175 Z3 L4 Q46 4176 Z3 L4 Q47 4177 Z3 L4 Q48 4178 Z3 L4 Q49 4179 Z3 L4 Q50 4180 Z3 L4 Q51 4181 Z3 L4 Q52 4182 Z3 L4 Q53 4183 Z3 L4 Q54 4184 Z3 L4 Q55 4185 Z3 L4 Q56 4186 Z3 L4 Q57 4187 Z3 L4 Q58 4188 Z3 L4 Q59 4189 Z3 L4 Q60 4190 Z3 L4 Q61 4191 Z3 L4 Q62 4192 Z3 L4 Q63 4193 Z3 L4 Q64

TABLE 1-27 4194 Z3 L4 Q65 4195 Z3 L4 Q66 4196 Z3 L4 Q67 4197 Z3 L4 Q68 4198 Z3 L4 Q69 4199 Z3 L4 Q70 4200 Z3 L4 Q71 4201 Z3 L4 Q72 4202 Z3 L4 Q73 4203 Z3 L4 Q74 4204 Z3 L4 Q75 4205 Z3 L4 Q76 4206 Z3 L4 Q77 4207 Z3 L4 Q78 4208 Z3 L4 Q79 4209 Z3 L4 Q80 4210 Z3 L4 Q81 4211 Z3 L4 Q82 4212 Z3 L4 Q83 4213 Z3 L4 Q84 4214 Z3 L4 Q85 4215 Z3 L4 Q86 4216 Z3 L4 Q87 4217 Z3 L4 Q88 4218 Z3 L4 Q89 4219 Z3 L4 Q90 4220 Z3 L4 Q91 4221 Z3 L4 Q92 4222 Z3 L4 Q93 4223 Z3 L4 Q94 4224 Z3 L4 Q95 4225 Z3 L4 Q96 4226 Z3 L4 Q97 4227 Z3 L4 Q98 4228 Z3 L4 Q99 4229 Z3 L4 Q100 4230 Z3 L4 Q101 4231 Z3 L4 Q102 4232 Z3 L4 Q103 4233 Z3 L5 Q40 4234 Z3 L5 Q41 4235 Z3 L5 Q42 4236 Z3 L5 Q43 4237 Z3 L5 Q44 4238 Z3 L5 Q45 4239 Z3 L5 Q46 4240 Z3 L5 Q47 4241 Z3 L5 Q48 4242 Z3 L5 Q49 4243 Z3 L5 Q50 4244 Z3 L5 Q51 4245 Z3 L5 Q52 4246 Z3 L5 Q53 4247 Z3 L5 Q54 4248 Z3 L5 Q55 4249 Z3 L5 Q56 4250 Z3 L5 Q57 4251 Z3 L5 Q58 4252 Z3 L5 Q59 4253 Z3 L5 Q60 4254 Z3 L5 Q61 4255 Z3 L5 Q62 4256 Z3 L5 Q63 4257 Z3 L5 Q64 4258 Z3 L5 Q65 4259 Z3 L5 Q66 4260 Z3 L5 Q67 4261 Z3 L5 Q68 4262 Z3 L5 Q69 4263 Z3 L5 Q70 4264 Z3 L5 Q71 4265 Z3 L5 Q72 4266 Z3 L5 Q73 4267 Z3 L5 Q74 4268 Z3 L5 Q75 4269 Z3 L5 Q76 4270 Z3 L5 Q77 4271 Z3 L5 Q78 4272 Z3 L5 Q79 4273 Z3 L5 Q80 4274 Z3 L5 Q81 4275 Z3 L5 Q82 4276 Z3 L5 Q83 4277 Z3 L5 Q84 4278 Z3 L5 Q85 4279 Z3 L5 Q86 4280 Z3 L5 Q87 4281 Z3 L5 Q88 4282 Z3 L5 Q89 4283 Z3 L5 Q90 4284 Z3 L5 Q91 4285 Z3 L5 Q92 4286 Z3 L5 Q93 4287 Z3 L5 Q94 4288 Z3 L5 Q95 4289 Z3 L5 Q96 4290 Z3 L5 Q97 4291 Z3 L5 Q98 4292 Z3 L5 Q99 4293 Z3 L5 Q100 4294 Z3 L5 Q101 4295 Z3 L5 Q102 4296 Z3 L5 Q103 4297 Z3 L6 Q40 4298 Z3 L6 Q41 4299 Z3 L6 Q42 4300 Z3 L6 Q43 4301 Z3 L6 Q44 4302 Z3 L6 Q45 4303 Z3 L6 Q46 4304 Z3 L6 Q47 4305 Z3 L6 Q48 4306 Z3 L6 Q49 4307 Z3 L6 Q50 4308 Z3 L6 Q51 4309 Z3 L6 Q52 4310 Z3 L6 Q53 4311 Z3 L6 Q54 4312 Z3 L6 Q55 4313 Z3 L6 Q56 4314 Z3 L6 Q57 4315 Z3 L6 Q58 4316 Z3 L6 Q59 4317 Z3 L6 Q60 4318 Z3 L6 Q61 4319 Z3 L6 Q62 4320 Z3 L6 Q63 4321 Z3 L6 Q64 4322 Z3 L6 Q65 4323 Z3 L6 Q66 4324 Z3 L6 Q67 4325 Z3 L6 Q68 4326 Z3 L6 Q69 4327 Z3 L6 Q70 4328 Z3 L6 Q71 4329 Z3 L6 Q72 4330 Z3 L6 Q73 4331 Z3 L6 Q74 4332 Z3 L6 Q75 4333 Z3 L6 Q76 4334 Z3 L6 Q77 4335 Z3 L6 Q78 4336 Z3 L6 Q79 4337 Z3 L6 Q80 4338 Z3 L6 Q81 4339 Z3 L6 Q82 4340 Z3 L6 Q83 4341 Z3 L6 Q84 4342 Z3 L6 Q85 4343 Z3 L6 Q86 4344 Z3 L6 Q87 4345 Z3 L6 Q88 4346 Z3 L6 Q89 4347 Z3 L6 Q90 4348 Z3 L6 Q91 4349 Z3 L6 Q92 4350 Z3 L6 Q93 4351 Z3 L6 Q94 4352 Z3 L6 Q95 4353 Z3 L6 Q96 4354 Z3 L6 Q97 4355 Z3 L6 Q98 4356 Z3 L6 Q99 4357 Z3 L6 Q100 4358 Z3 L6 Q101 4359 Z3 L6 Q102 4360 Z3 L6 Q103 4361 Z3 L7 Q40 4362 Z3 L7 Q41 4363 Z3 L7 Q42 4364 Z3 L7 Q43 4365 Z3 L7 Q44 4366 Z3 L7 Q45 4367 Z3 L7 Q46 4368 Z3 L7 Q47 4369 Z3 L7 Q48 4370 Z3 L7 Q49 4371 Z3 L7 Q50 4372 Z3 L7 Q51 4373 Z3 L7 Q52 4374 Z3 L7 Q53 4375 Z3 L7 Q54 4376 Z3 L7 Q55 4377 Z3 L7 Q56 4378 Z3 L7 Q57 4379 Z3 L7 Q58 4380 Z3 L7 Q59 4381 Z3 L7 Q60 4382 Z3 L7 Q61 4383 Z3 L7 Q62 4384 Z3 L7 Q63 4385 Z3 L7 Q64 4386 Z3 L7 Q65 4387 Z3 L7 Q66 4388 Z3 L7 Q67 4389 Z3 L7 Q68 4390 Z3 L7 Q69 4391 Z3 L7 Q70 4392 Z3 L7 Q71 4393 Z3 L7 Q72 4392 Z3 L7 Q73

TABLE 1-28 4395 Z3 L7 Q74 4396 Z3 L7 Q75 4397 Z3 L7 Q76 4398 Z3 L7 Q77 4399 Z3 L7 Q78 4400 Z3 L7 Q79 4401 Z3 L7 Q80 4402 Z3 L7 Q81 4403 Z3 L7 Q82 4404 Z3 L7 Q83 4405 Z3 L7 Q84 4406 Z3 L7 Q85 4407 Z3 L7 Q86 4408 Z3 L7 Q87 4409 Z3 L7 Q88 4410 Z3 L7 Q89 4411 Z3 L7 Q90 4412 Z3 L7 Q91 4413 Z3 L7 Q92 4414 Z3 L7 Q93 4415 Z3 L7 Q94 4416 Z3 L7 Q95 4417 Z3 L7 Q96 4418 Z3 L7 Q97 4419 Z3 L7 Q98 4420 Z3 L7 Q99 4421 Z3 L7 Q100 4422 Z3 L7 Q101 4423 Z3 L7 Q102 4424 Z3 L7 Q103 4425 Z3 L8 Q40 4426 Z3 L8 Q41 4427 Z3 L8 Q42 4428 Z3 L8 Q43 4429 Z3 L8 Q44 4430 Z3 L8 Q45 4431 Z3 L8 Q46 4432 Z3 L8 Q47 4433 Z3 L8 Q48 4434 Z3 L8 Q49 4435 Z3 L8 Q50 4436 Z3 L8 Q51 4437 Z3 L8 Q52 4438 Z3 L8 Q53 4439 Z3 L8 Q54 4440 Z3 L8 Q55 4441 Z3 L8 Q56 4442 Z3 L8 Q57 4443 Z3 L8 Q58 4444 Z3 L8 Q59 4445 Z3 L8 Q60 4446 Z3 L8 Q61 4447 Z3 L8 Q62 4448 Z3 L8 Q63 4449 Z3 L8 Q64 4450 Z3 L8 Q65 4451 Z3 L8 Q66 4452 Z3 L8 Q67 4453 Z3 L8 Q68 4454 Z3 L8 Q69 4455 Z3 L8 Q70 4456 Z3 L8 Q71 4457 Z3 L8 Q72 4458 Z3 L8 Q73 4459 Z3 L8 Q74 4460 Z3 L8 Q75 4461 Z3 L8 Q76 4462 Z3 L8 Q77 4463 Z3 L8 Q78 4464 Z3 L8 Q79 4465 Z3 L8 Q80 4466 Z3 L8 Q81 4467 Z3 L8 Q82 4468 Z3 L8 Q83 4469 Z3 L8 Q84 4470 Z3 L8 Q85 4471 Z3 L8 Q86 4472 Z3 L8 Q87 4473 Z3 L8 Q88 4474 Z3 L8 Q89 4475 Z3 L8 Q90 4476 Z3 L8 Q91 4477 Z3 L8 Q92 4478 Z3 L8 Q93 4479 Z3 L8 Q94 4480 Z3 L8 Q95 4481 Z3 L8 Q96 4482 Z3 L8 Q97 4483 Z3 L8 Q98 4484 Z3 L8 Q99 4485 Z3 L8 Q100 4486 Z3 L8 Q101 4487 Z3 L8 Q102 4488 Z3 L8 Q103 4489 Z3 L9 Q40 4490 Z3 L9 Q41 4491 Z3 L9 Q42 4492 Z3 L9 Q43 4493 Z3 L9 Q44 4494 Z3 L9 Q45 4495 Z3 L9 Q46 4496 Z3 L9 Q47 4497 Z3 L9 Q48 4498 Z3 L9 Q49 4499 Z3 L9 Q50 4500 Z3 L9 Q51 4501 Z3 L9 Q52 4502 Z3 L9 Q53 4503 Z3 L9 Q54 4504 Z3 L9 Q55 4505 Z3 L9 Q56 4506 Z3 L9 Q57 4507 Z3 L9 Q58 4508 Z3 L9 Q59 4509 Z3 L9 Q60 4510 Z3 L9 Q61 4511 Z3 L9 Q62 4512 Z3 L9 Q63 4513 Z3 L9 Q64 4514 Z3 L9 Q65 4515 Z3 L9 Q66 4516 Z3 L9 Q67 4517 Z3 L9 Q68 4518 Z3 L9 Q69 4519 Z3 L9 Q70 4520 Z3 L9 Q71 4521 Z3 L9 Q72 4522 Z3 L9 Q73 4523 Z3 L9 Q74 4524 Z3 L9 Q75 4525 Z3 L9 Q76 4526 Z3 L9 Q77 4527 Z3 L9 Q78 4528 Z3 L9 Q79 4529 Z3 L9 Q80 4530 Z3 L9 Q81 4531 Z3 L9 Q82 4532 Z3 L9 Q83 4533 Z3 L9 Q84 4534 Z3 L9 Q85 4535 Z3 L9 Q86 4536 Z3 L9 Q87 4537 Z3 L9 Q88 4538 Z3 L9 Q89 4539 Z3 L9 Q90 4540 Z3 L9 Q91 4541 Z3 L9 Q92 4542 Z3 L9 Q93 4543 Z3 L9 Q94 4544 Z3 L9 Q95 4545 Z3 L9 Q96 4546 Z3 L9 Q97 4547 Z3 L9 Q98 4548 Z3 L9 Q99 4549 Z3 L9 Q100 4550 Z3 L9 Q101 4551 Z3 L9 Q102 4552 Z3 L9 Q103 4553 Z3 L10 Q40 4554 Z3 L10 Q41 4555 Z3 L10 Q42 4556 Z3 L10 Q43 4557 Z3 L10 Q44 4558 Z3 L10 Q45 4559 Z3 L10 Q46 4560 Z3 L10 Q47 4561 Z3 L10 Q48 4562 Z3 L10 Q49 4563 Z3 L10 Q50 4564 Z3 L10 Q51 4565 Z3 L10 Q52 4566 Z3 L10 Q53 4567 Z3 L10 Q54 4568 Z3 L10 Q55 4569 Z3 L10 Q56 4570 Z3 L10 Q57 4571 Z3 L10 Q58 4572 Z3 L10 Q59 4573 Z3 L10 Q60 4574 Z3 L10 Q61 4575 Z3 L10 Q62 4576 Z3 L10 Q63 4577 Z3 L10 Q64 4578 Z3 L10 Q65 4579 Z3 L10 Q66 4580 Z3 L10 Q67 4581 Z3 L10 Q68 4582 Z3 L10 Q69 4583 Z3 L10 Q70 4584 Z3 L10 Q71 4585 Z3 L10 Q72 4586 Z3 L10 Q73 4587 Z3 L10 Q74 4588 Z3 L10 Q75 4589 Z3 L10 Q76 4590 Z3 L10 Q77 4591 Z3 L10 Q78 4592 Z3 L10 Q79 4593 Z3 L10 Q80 4594 Z3 L10 Q81 4595 Z3 L10 Q82

TABLE 1-29 4596 Z3 L10 Q83 4597 Z3 L10 Q84 4598 Z3 L10 Q85 4599 Z3 L10 Q86 4600 Z3 L10 Q87 4601 Z3 L10 Q88 4602 Z3 L10 Q89 4603 Z3 L10 Q90 4604 Z3 L10 Q91 4605 Z3 L10 Q92 4606 Z3 L10 Q93 4607 Z3 L10 Q94 4608 Z3 L10 Q95 4609 Z3 L10 Q96 4610 Z3 L10 Q97 4611 Z3 L10 Q98 4612 Z3 L10 Q99 4613 Z3 L10 Q100 4614 Z3 L10 Q101 4615 Z3 L10 Q102 4616 Z3 L10 Q103 4617 Z3 L11 Q40 4618 Z3 L11 Q41 4619 Z3 L11 Q42 4620 Z3 L11 Q43 4621 Z3 L11 Q44 4622 Z3 L11 Q45 4623 Z3 L11 Q46 4624 Z3 L11 Q47 4625 Z3 L11 Q43 4626 Z3 L11 Q49 4627 Z3 L11 Q50 4628 Z3 L11 Q51 4629 Z3 L11 Q52 4630 Z3 L11 Q53 4634 Z3 L11 Q54 4632 Z3 L11 Q55 4633 Z3 L11 Q56 4634 Z3 L11 Q57 4635 Z3 L11 Q58 4636 Z3 L11 Q59 4637 Z3 L11 Q60 4638 Z3 L11 Q61 4639 Z3 L11 Q62 4640 Z3 L11 Q63 4641 Z3 L11 Q64 4642 Z3 L11 Q65 4643 Z3 L11 Q66 4644 Z3 L11 Q67 4645 Z3 L11 Q68 4646 Z3 L11 Q69 4647 Z3 L11 Q70 4648 Z3 L11 Q71 4649 Z3 L11 Q72 4650 Z3 L11 Q73 4651 Z3 L11 Q74 4652 Z3 L11 Q75 4653 Z3 L11 Q76 4654 Z3 L11 Q77 4655 Z3 L11 Q78 4656 Z3 L11 Q79 4657 Z3 L11 Q80 4658 Z3 L11 Q81 4659 Z3 L11 Q82 4660 Z3 L11 Q83 4661 Z3 L11 Q84 4662 Z3 L11 Q85 4663 Z3 L11 Q86 4664 Z3 L11 Q87 4665 Z3 L11 Q88 4666 Z3 L11 Q89 4667 Z3 L11 Q90 4668 Z3 L11 Q91 4669 Z3 L11 Q92 4670 Z3 L11 Q93 4671 Z3 L11 Q94 4672 Z3 L11 Q95 4673 Z3 L11 Q96 4674 Z3 L11 Q97 4675 Z3 L11 Q98 4676 Z3 L11 Q99 4677 Z3 L11 Q100 4678 Z3 L11 Q101 4679 Z3 L11 Q102 4680 Z3 L11 Q103 4681 Z3 L12 Q40 4682 Z3 L12 Q41 4683 Z3 L12 Q42 4684 Z3 L12 Q43 4685 Z3 L12 Q44 4686 Z3 L12 Q45 4687 Z3 L12 Q46 4688 Z3 L12 Q47 4689 Z3 L12 Q48 4690 Z3 L12 Q49 4691 Z3 L12 Q50 4692 Z3 L12 Q51 4693 Z3 L12 Q52 4694 Z3 L12 Q53 4695 Z3 L12 Q54 4696 Z3 L12 Q55 4697 Z3 L12 Q56 4698 Z3 L12 Q57 4699 Z3 L12 Q58 4700 Z3 L12 Q59 4701 Z3 L12 Q60 4702 Z3 L12 Q61 4703 Z3 L12 Q62 4704 Z3 L12 Q63 4705 Z3 L12 Q64 4706 Z3 L12 Q65 4707 Z3 L12 Q66 4708 Z3 L12 Q67 4709 Z3 L12 Q68 4710 Z3 L12 Q69 4711 Z3 L12 Q70 4712 Z3 L12 Q71 4713 Z3 L12 Q72 4714 Z3 L12 Q73 4715 Z3 L12 Q74 4716 Z3 L12 Q75 4717 Z3 L12 Q76 4718 Z3 L12 Q77 4719 Z3 L12 Q78 4720 Z3 L12 Q79 4721 Z3 L12 Q80 4722 Z3 L12 Q81 4723 Z3 L12 Q82 4724 Z3 L12 Q83 4725 Z3 L12 Q84 4726 Z3 L12 Q85 4727 Z3 L12 Q86 4728 Z3 L12 Q87 4729 Z3 L12 Q88 4730 Z3 L12 Q89 4731 Z3 L12 Q90 4732 Z3 L12 Q91 4733 Z3 L12 Q92 4734 Z3 L12 Q93 4735 Z3 L12 Q94 4736 Z3 L12 Q95 4737 Z3 L12 Q96 4738 Z3 L12 Q97 4739 Z3 L12 Q98 4740 Z3 L12 Q99 4741 Z3 L12 Q100 4742 Z3 L12 Q101 4743 Z3 L12 Q102 4744 Z3 L12 Q103 4745 Z3 L13 Q40 4746 Z3 L13 Q41 4747 Z3 L13 Q42 4748 Z3 L13 Q43 4749 Z3 L13 Q44 4750 Z3 L13 Q45 4751 Z3 L13 Q46 4752 Z3 L13 Q47 4753 Z3 L13 Q48 4754 Z3 L13 Q49 4755 Z3 L13 Q50 4756 Z3 L13 Q51 4757 Z3 L13 Q52 4758 Z3 L13 Q53 4759 Z3 L13 Q54 4760 Z3 L13 Q55 4761 Z3 L13 Q56 4762 Z3 L13 Q57 4763 Z3 L13 Q58 4764 Z3 L13 Q59 4765 Z3 L13 Q60 4766 Z3 L13 Q61 4767 Z3 L13 Q62 4768 Z3 L13 Q63 4769 Z3 L13 Q64 4770 Z3 L13 Q65 4771 Z3 L13 Q66 4772 Z3 L13 Q67 4773 Z3 L13 Q68 4774 Z3 L13 Q69 4775 Z3 L13 Q70 4776 Z3 L13 Q71 4777 Z3 L13 Q72 4778 Z3 L13 Q73 4779 Z3 L13 Q74 4780 Z3 L13 Q75 4781 Z3 L13 Q76 4782 Z3 L13 Q77 4783 Z3 L13 Q78 4784 Z3 L13 Q79 4785 Z3 L13 Q80 4786 Z3 L13 Q71 4787 Z3 L13 Q72 4788 Z3 L13 Q73 4789 Z3 L13 Q74 4890 Z3 L13 Q75 4891 Z3 L13 Q76 4892 Z3 L13 Q77 4893 Z3 L13 Q78 4894 Z3 L13 Q79 4895 Z3 L13 Q80 4896 Z3 L13 Q81

TABLE 1-30 4797 Z3 L13 Q92 4798 Z3 L13 Q93 4799 Z3 L13 Q94 4800 Z3 L13 Q95 4801 Z3 L13 Q96 4802 Z3 L13 Q97 4803 Z3 L13 Q98 4604 Z3 L13 Q99 4805 Z3 L13 Q100 4806 Z3 L13 Q101 4807 Z3 L13 Q102 4808 Z3 L13 Q103 4809 Z3 L14 Q40 4810 Z3 L14 Q41 4811 Z3 L14 Q42 4312 Z3 L14 Q43 4813 Z3 L14 Q44 4814 Z3 L14 Q45 4815 Z3 L14 Q46 4816 Z3 L14 Q47 4817 Z3 L14 Q48 4818 Z3 L14 Q49 4819 Z3 L14 Q50 4820 Z3 L14 Q51 4821 Z3 L14 Q52 4822 Z3 L14 Q53 4823 Z3 L14 Q54 4824 Z3 L14 Q55 4825 Z3 L14 Q56 4826 Z3 L14 Q57 4827 Z3 L14 Q58 4828 Z3 L14 Q59 4829 Z3 L14 Q60 4830 Z3 L14 Q61 4831 Z3 L14 Q62 4832 Z3 L14 Q63 4833 Z3 L14 Q64 4834 Z3 L14 Q65 4835 Z3 L14 Q66 4836 Z3 L14 Q67 4837 Z3 L14 Q68 4838 Z3 L14 Q69 4839 Z3 L14 Q70 4840 Z3 L14 Q71 4841 Z3 L14 Q72 4842 Z3 L14 Q73 4843 Z3 L14 Q74 4844 Z3 L14 Q75 4845 Z3 L14 Q76 4846 Z3 L14 Q77 4847 Z3 L14 Q78 4848 Z3 L14 Q79 4849 Z3 L14 Q80 4850 Z3 L14 Q81 4851 Z3 L14 Q82 4852 Z3 L14 Q83 4853 Z3 L14 Q84 4854 Z3 L14 Q85 4855 Z3 L14 Q86 4856 Z3 L14 Q87 4857 Z3 L14 Q88 4858 Z3 L14 Q89 4859 Z3 L14 Q90 4860 Z3 L14 Q91 4861 Z3 L14 Q92 4862 Z3 L14 Q93 4863 Z3 L14 Q94 4864 Z3 L14 Q95 4665 Z3 L14 Q96 4866 Z3 L14 Q97 4867 Z3 L14 Q98 4868 Z3 L14 Q99 4869 Z3 L14 Q100 4970 Z3 L14 Q101 4371 Z3 L14 Q102 4872 Z3 L14 Q103 4873 Z4 L1 Q40 4874 Z4 L1 Q41 48/5 Z4 L1 Q42 4876 Z4 L1 Q43 4877 Z4 L1 Q44 4878 Z4 L1 Q45 4879 Z4 L1 Q46 4880 Z4 L1 Q47 4881 Z4 L1 Q48 4682 Z4 L1 Q40 4883 Z4 L1 Q50 4884 Z4 L1 Q51 4885 Z4 L1 Q52 4886 Z4 L1 Q53 4887 Z4 L1 Q54 4888 Z4 L1 Q55 4889 Z4 L1 Q56 4890 Z4 L1 Q57 4891 Z4 L1 Q58 4892 Z4 L1 Q59 4893 Z4 L1 Q60 4894 Z4 L1 Q61 4895 Z4 L1 Q62 4896 Z4 L1 Q63 4897 Z4 L1 Q64 4898 Z4 L1 Q65 4899 Z4 L1 Q66 4900 Z4 L1 Q67 4901 Z4 L1 Q68 4902 Z4 L1 Q69 4903 Z4 L1 Q70 4904 Z4 L1 Q71 4905 Z4 L1 Q72 4906 Z4 L1 Q73 4907 Z4 L1 Q74 4908 Z4 L1 Q75 4909 Z4 L1 Q76 4910 Z4 L1 Q77 4911 Z4 L1 Q78 4912 Z4 L1 Q79 4913 Z4 L1 Q80 4914 Z4 L1 Q81 4915 Z4 L1 Q82 4916 Z4 L1 Q83 4917 Z4 L1 Q84 4918 Z4 L1 Q85 4919 Z4 L1 Q86 4920 Z4 L1 Q87 4921 Z4 L1 Q88 4922 Z4 L1 Q89 4923 Z4 L1 Q90 4924 Z4 L1 Q91 4925 Z4 L1 Q92 4926 Z4 L1 Q93 4927 Z4 L1 Q94 4928 Z4 L1 Q95 4929 Z4 L1 Q96 4930 Z4 L1 Q97 4931 Z4 L1 Q98 4932 Z4 L1 Q99 4933 Z4 L1 Q100 4934 Z4 L1 Q101 4935 Z4 L1 Q102 4936 Z4 L1 Q103 4937 Z4 L2 Q40 4938 Z4 L2 Q41 4939 Z4 L2 Q42 4940 Z4 L2 Q43 4941 Z4 L2 Q44 4942 Z4 L2 Q45 4943 Z4 L2 Q46 4944 Z4 L2 0147 4945 Z4 L2 Q48 4946 Z4 L2 Q49 4947 Z4 L2 Q50 4948 Z4 L2 Q51 4049 Z4 L2 Q52 4950 Z4 L2 Q53 4951 Z4 L2 Q54 4952 Z4 L2 Q55 4953 Z4 L2 Q56 4954 Z4 L2 Q57 4955 Z4 L2 Q58 4956 Z4 L2 Q59 4957 Z4 L2 Q60 4958 Z4 L2 Q61 4959 Z4 L2 Q62 4960 Z4 L2 Q63 4961 Z4 L2 Q64 4962 Z4 L2 Q65 4963 Z4 L2 Q66 4964 Z4 L2 Q67 4965 Z4 L2 Q68 4066 Z4 L2 Q69 4967 Z4 L2 Q70 4968 Z4 L2 Q71 4969 Z4 L2 Q72 4970 Z4 L2 Q73 4971 Z4 L2 Q74 4972 Z4 L2 Q75 4973 Z4 L2 Q76 4974 Z4 L2 Q77 4975 Z4 L2 Q78 4976 Z4 L2 Q79 4977 Z4 L2 Q80 4978 Z4 L2 Q81 4979 Z4 L2 Q82 4980 Z4 L2 Q83 4981 Z4 L2 Q84 4982 Z4 L2 Q85 4983 Z4 L2 Q86 4984 Z4 L2 Q87 4985 Z4 L2 Q88 4986 Z4 L2 Q89 4987 Z4 L2 Q90 4988 Z4 L2 Q91 4989 Z4 L2 Q92 4990 Z4 L2 Q93 4991 Z4 L2 Q94 4992 Z4 L2 Q95 4993 Z4 L2 Q96 4994 Z4 L2 Q97 4995 Z4 L2 Q98 4996 Z4 L2 Q99 4997 Z4 L2 Q100

TABLE 1-31 4993 Z4 L2 Q101 4999 Z4 L2 Q102 5000 Z4 L2 Q103 5001 Z4 L3 Q40 5002 Z4 L3 Q41 5003 Z4 L3 Q42 5004 Z4 L3 Q43 5005 Z4 L3 Q44 5006 Z4 L3 Q45 5007 Z4 L3 Q46 5008 Z4 L3 Q47 5009 Z4 L3 Q48 5010 Z4 L3 Q49 5011 Z4 L3 Q50 5012 Z4 L3 Q51 5013 Z4 L3 Q52 5014 Z4 L3 Q53 5015 Z4 L3 Q54 5016 Z4 L3 Q55 5017 Z4 L3 Q56 5018 Z4 L3 Q57 5019 Z4 L3 Q58 5020 Z4 L3 Q59 5021 Z4 L3 Q60 5022 Z4 L3 Q61 5023 Z4 L3 Q62 5024 Z4 L3 Q63 5025 Z4 L3 Q64 5026 Z4 L3 Q65 5027 Z4 L3 Q66 5028 Z4 L3 Q67 5029 Z4 L3 Q68 5030 Z4 L3 Q69 5031 Z4 L3 Q70 5032 Z4 L3 Q71 5033 Z4 L3 Q72 5034 Z4 L3 Q73 5035 Z4 L3 Q74 5036 Z4 L3 Q75 5037 Z4 L3 Q76 5033 Z4 L3 Q77 5039 Z4 L3 Q78 5040 Z4 L3 Q79 5041 Z4 L3 Q80 5042 Z4 L3 Q81 5043 Z4 L3 Q82 5044 Z4 L3 Q83 5045 Z4 L3 Q84 5046 Z4 L3 Q85 5047 Z4 L3 Q86 5048 Z4 L3 Q87 5049 Z4 L3 Q88 5050 Z4 L3 Q89 5051 Z4 L3 Q90 5052 Z4 L3 Q91 5053 Z4 L3 Q92 5054 Z4 L3 Q93 5055 Z4 L3 Q94 5056 Z4 L3 Q95 5057 Z4 L3 Q96 5058 Z4 L3 Q97 5059 Z4 L3 Q98 5060 Z4 L3 Q99 5061 Z4 L3 Q100 5062 Z4 L3 Q101 5063 Z4 L3 Q102 5064 Z4 L3 Q103 5065 Z4 Z4 Q40 5066 Z4 Z4 Q41 5067 Z4 Z4 Q42 5068 Z4 Z4 Q43 5069 Z4 Z4 Q44 5070 Z4 Z4 Q45 5071 Z4 Z4 Q46 5072 Z4 Z4 Q47 5073 Z4 Z4 Q48 5074 Z4 Z4 Q49 5075 Z4 Z4 Q50 5076 Z4 Z4 Q51 5077 Z4 Z4 Q52 5078 Z4 Z4 Q53 5079 Z4 Z4 Q54 5080 Z4 Z4 Q55 5081 Z4 Z4 Q56 5082 Z4 Z4 Q57 5063 Z4 Z4 Q58 5084 Z4 Z4 Q59 5085 Z4 Z4 Q60 50E6 Z4 Z4 Q61 5087 Z4 Z4 Q62 50E8 Z4 Z4 Q63 5069 Z4 Z4 Q64 5090 Z4 Z4 Q65 5091 Z4 Z4 Q66 5092 Z4 Z4 Q67 5093 Z4 Z4 Q68 5094 Z4 Z4 Q69 5095 Z4 Z4 Q70 5096 Z4 Z4 Q71 5097 Z4 Z4 Q72 5098 Z4 Z4 Q73 5099 Z4 Z4 Q74 5100 Z4 Z4 Q75 5101 Z4 Z4 Q76 5102 Z4 Z4 Q77 5103 Z4 Z4 Q78 5104 Z4 Z4 Q79 5105 Z4 Z4 Q80 5106 Z4 Z4 Q81 5107 Z4 Z4 Q82 5108 Z4 Z4 Q83 5109 Z4 Z4 Q84 5110 Z4 Z4 Q85 5111 Z4 Z4 Q86 5112 Z4 Z4 Q87 5113 Z4 Z4 Q88 5114 Z4 Z4 Q89 5115 Z4 Z4 Q90 5116 Z4 Z4 Q91 5117 Z4 Z4 Q92 5118 Z4 Z4 Q93 5119 Z4 Z4 Q94 5120 Z4 Z4 Q95 5121 Z4 Z4 Q96 5122 Z4 Z4 Q97 5123 Z4 Z4 Q98 5124 Z4 Z4 Q99 5125 Z4 Z4 Q100 5126 Z4 Z4 Q101 5127 Z4 Z4 Q102 5128 Z4 Z4 Q103 5129 Z4 L5 Q40 5130 Z4 L5 Q41 5131 Z4 L5 Q42 5132 Z4 L5 Q43 5133 Z4 L5 Q44 5134 Z4 L5 Q45 5135 Z4 L5 Q46 5136 Z4 L5 Q47 5137 Z4 L5 Q48 5138 Z4 L5 Q49 5139 Z4 L5 Q50 5140 Z4 L5 Q51 5141 Z4 L5 Q52 5142 Z4 L5 Q53 5143 Z4 L5 Q54 5144 Z4 L5 Q55 5145 Z4 L5 Q56 5146 Z4 L5 Q57 5147 Z4 L5 Q58 5148 Z4 L5 Q59 5149 Z4 L5 Q60 5150 Z4 L5 Q61 5151 Z4 L5 Q62 5152 Z4 L5 Q63 5153 Z4 L5 Q64 5154 Z4 L5 Q65 5155 Z4 L5 Q66 5156 Z4 L5 Q67 5157 Z4 L5 Q68 5158 Z4 L5 Q69 5159 Z4 L5 Q70 5160 Z4 L5 Q71 5161 Z4 L5 Q72 5162 Z4 L5 Q73 5163 Z4 L5 Q74 5164 Z4 L5 Q75 5165 Z4 L5 Q76 5166 Z4 L5 Q77 5167 Z4 L5 Q78 5168 Z4 L5 Q79 5169 Z4 L5 Q80 5170 Z4 L5 Q81 5171 Z4 L5 Q82 5172 Z4 L5 Q83 5173 Z4 L5 Q84 5174 Z4 L5 Q85 5175 Z4 L5 Q86 5176 Z4 L5 Q87 5177 Z4 L5 Q88 5178 Z4 L5 Q89 5179 Z4 L5 Q90 5180 Z4 L5 Q91 5181 Z4 L5 Q92 5182 Z4 L5 Q93 5183 Z4 L5 Q94 5184 Z4 L5 Q95 5185 Z4 L5 Q96 5186 Z4 L5 Q97 5187 Z4 L5 Q98 5188 Z4 L5 Q99 5189 Z4 L5 Q100 5190 Z4 L5 Q101 5191 Z4 L5 Q102 5192 Z4 L5 Q103 5193 Z4 L6 Q40 5194 Z4 L6 Q41 5195 Z4 L6 Q42 5196 Z4 L6 Q43 5197 Z4 L6 Q44 5198 Z4 L6 Q45

TABLE 1-32 5199 Z4 L6 Q46 5200 Z4 L6 Q47 5201 Z4 L6 Q48 5202 Z4 L6 Q49 5263 Z4 L6 Q50 5204 Z4 L6 Q51 5205 Z4 L6 Q52 5206 Z4 L6 Q53 5207 Z4 L6 Q54 5208 Z4 L6 Q55 5209 Z4 L6 Q56 5210 Z4 L6 Q57 5211 Z4 L6 Q58 5212 Z4 L6 Q59 5213 Z4 L6 Q60 5244 Z4 L6 Q61 5215 Z4 L6 Q62 5216 Z4 L6 Q63 5217 Z4 L6 Q64 5218 Z4 L6 Q65 5219 Z4 L6 Q66 5220 Z4 L6 Q67 5221 Z4 L6 Q68 5222 Z4 L6 Q69 5223 Z4 L6 Q70 5224 Z4 L6 Q71 5225 Z4 L6 Q72 5226 Z4 L6 Q73 5227 Z4 L6 Q74 5228 Z4 L6 Q75 5229 Z4 L6 Q76 5230 Z4 L6 Q77 5231 Z4 L6 Q78 5232 Z4 L6 Q79 5233 Z4 L6 Q80 5234 Z4 L6 Q81 5235 Z4 L6 Q82 5236 Z4 L6 Q83 5237 Z4 L6 Q84 5238 Z4 L6 Q85 5239 Z4 L6 Q86 5240 Z4 L6 Q87 5241 Z4 L6 Q88 5242 Z4 L6 Q89 5243 Z4 L6 Q90 5244 Z4 L6 Q91 5245 Z4 L6 Q92 5246 Z4 L6 Q93 5247 Z4 L6 Q94 5248 Z4 L6 Q95 5249 Z4 L6 Q96 5250 Z4 L6 Q97 5251 Z4 L6 Q98 5252 Z4 L6 Q99 5253 Z4 L6 Q100 5254 Z4 L6 Q101 5255 Z4 L6 Q102 5256 Z4 L6 Q103 5257 Z4 L7 Q40 5258 Z4 L7 Q41 5259 Z4 L7 Q42 5260 Z4 L7 Q43 5261 Z4 L7 Q44 5262 Z4 L7 Q45 5263 Z4 L7 Q46 5264 Z4 L7 Q47 5265 Z4 L7 Q48 5266 Z4 L7 Q49 5267 Z4 L7 Q50 5268 Z4 L7 Q51 5269 Z4 L7 Q52 5270 Z4 L7 Q53 5271 Z4 L7 Q54 5272 Z4 L7 Q55 5273 Z4 L7 Q56 5274 Z4 L7 Q57 5275 Z4 L7 Q58 5276 Z4 L7 Q59 5277 Z4 L7 Q60 5278 Z4 L7 Q61 5279 Z4 L7 Q62 5280 Z4 L7 Q63 5281 Z4 L7 Q64 5282 Z4 L7 Q65 5283 Z4 L7 Q66 5284 Z4 L7 Q67 5285 Z4 L7 Q68 5286 Z4 L7 Q69 5287 Z4 L7 Q70 5288 Z4 L7 Q71 5289 Z4 L7 Q72 5290 Z4 L7 Q73 5291 Z4 L7 Q74 5292 Z4 L7 Q75 5293 Z4 L7 Q76 5294 Z4 L7 Q77 5295 Z4 L7 Q78 5296 Z4 L7 Q79 5297 Z4 L7 Q80 5298 Z4 L7 Q81 5299 Z4 L7 Q82 5300 Z4 L7 Q83 5301 Z4 L7 Q84 5302 Z4 L7 Q85 5303 Z4 L7 Q86 5304 Z4 L7 Q87 5305 Z4 L7 Q88 5306 Z4 L7 Q89 5307 Z4 L7 Q90 5308 Z4 L7 Q91 5309 Z4 L7 Q92 5310 Z4 L7 Q93 5311 Z4 L7 Q94 5312 Z4 L7 Q95 5313 Z4 L7 Q96 5314 Z4 L7 Q97 5315 Z4 L7 Q98 5316 Z4 L7 Q99 5317 Z4 L7 Q100 5318 Z4 L7 Q101 5319 Z4 L7 Q102 5320 Z4 L7 Q103 5321 Z4 L7 Q40 5322 Z4 L7 Q41 5323 Z4 L7 Q42 5324 Z4 L7 Q43 5325 Z4 L7 Q44 5326 Z4 L7 Q45 5327 Z4 L7 Q46 5328 Z4 L7 Q47 5329 Z4 L7 Q48 5330 Z4 L7 Q49 5331 Z4 L7 Q50 5332 Z4 L7 Q51 5333 Z4 L8 Q52 5334 Z4 L8 Q53 5335 Z4 L8 Q54 5336 Z4 L8 Q55 5337 Z4 L8 Q56 5338 Z4 L8 Q57 5339 Z4 L8 Q58 5340 Z4 L8 Q59 5341 Z4 L8 Q60 5342 Z4 L8 Q61 5343 Z4 L8 Q62 5344 Z4 L8 Q63 5345 Z4 L8 Q64 5346 Z4 L8 Q65 5347 Z4 L8 Q66 5348 Z4 L8 Q67 5349 Z4 L8 Q68 5350 Z4 L8 Q69 5351 Z4 L8 Q70 5352 Z4 L8 Q71 5353 Z4 L8 Q72 5354 Z4 L8 Q73 5355 Z4 L8 Q74 5356 Z4 L8 Q75 5357 Z4 L8 Q76 5358 Z4 L8 Q77 5359 Z4 L8 Q78 5360 Z4 L8 Q79 5361 Z4 L8 Q80 5362 Z4 L8 Q81 5363 Z4 L8 Q82 5364 Z4 L8 Q83 5365 Z4 L8 Q84 5366 Z4 L8 Q85 5367 Z4 L8 Q86 5368 Z4 L8 Q87 5369 Z4 L8 Q88 5370 Z4 L8 Q89 5371 Z4 L8 Q90 5372 Z4 L8 Q91 5373 Z4 L8 Q92 5374 Z4 L8 Q93 5375 Z4 L8 Q94 5376 Z4 L8 Q95 5377 Z4 L8 Q96 5378 Z4 L8 Q97 5379 Z4 L8 Q98 5380 Z4 L8 Q99 5381 Z4 L8 Q100 5382 Z4 L8 Q101 5383 Z4 L8 Q102 5384 Z4 L8 Q103 5385 Z4 L9 Q40 5386 Z4 L9 Q41 5387 Z4 L9 Q42 5388 Z4 L9 Q43 5389 Z4 L9 Q44 5390 Z4 L9 Q45 5391 Z4 L9 Q46 5392 Z4 L9 Q47 5393 Z4 L9 Q48 5394 Z4 L9 Q49 5395 Z4 L9 Q50 5396 Z4 L9 Q51 5397 Z4 L9 Q52 5398 Z4 L9 Q53 5399 Z4 L9 Q54

TABLE 1-33 5400 Z4 L9 Q55 5401 Z4 L9 Q56 5402 Z4 L9 Q57 5403 Z4 L9 Q58 5404 Z4 L9 Q59 5405 Z4 L9 Q60 5406 Z4 L9 Q61 5407 Z4 L9 Q62 5408 Z4 L9 Q63 5409 Z4 L9 Q64 5410 Z4 L9 Q65 5411 Z4 L9 Q66 5412 Z4 L9 Q67 5413 Z4 L9 Q68 5414 Z4 L9 Q69 5415 Z4 L9 Q70 5416 Z4 L9 Q71 5417 Z4 L9 Q72 5418 Z4 L9 Q73 5419 Z4 L9 Q74 5420 Z4 L9 Q75 5421 Z4 L9 Q76 5422 Z4 L9 Q77 5423 Z4 L9 Q78 5424 Z4 L9 Q79 5425 Z4 L9 Q80 5426 Z4 L9 Q81 5427 Z4 L9 Q82 5428 Z4 L9 Q83 5429 Z4 L9 Q84 5430 Z4 L9 Q85 5431 Z4 L9 Q86 5432 Z4 L9 Q87 5433 Z4 L9 Q88 5434 Z4 L9 Q89 5435 Z4 L9 Q90 5436 Z4 L9 Q91 5437 Z4 L9 Q92 5439 Z4 L9 Q93 5439 Z4 L9 Q94 5440 Z4 L9 Q95 5441 Z4 L9 Q96 5442 Z4 L9 Q97 5443 Z4 L9 Q98 5444 Z4 L9 Q99 5445 Z4 L9 Q100 5446 Z4 L9 Q101 5447 Z4 L9 Q102 5448 Z4 L9 Q103 5449 Z4 L10 Q40 5450 Z4 L10 Q41 5451 Z4 L10 Q42 5452 Z4 L10 Q43 5453 Z4 L10 Q44 5454 Z4 L10 Q45 5455 Z4 L10 Q46 5456 Z4 L10 Q47 5457 Z4 L10 Q48 5458 Z4 L10 Q49 5459 Z4 L10 Q50 5460 Z4 L10 Q51 5461 Z4 L10 Q52 5462 Z4 L10 Q53 5463 Z4 L10 Q54 5464 Z4 L10 Q55 5465 Z4 L10 Q56 5466 Z4 L10 Q57 5467 Z4 L10 Q58 5468 Z4 L10 Q59 5469 Z4 L10 Q60 5470 Z4 L10 Q61 5471 Z4 L10 Q62 5472 Z4 L10 Q63 5473 Z4 L10 Q64 5474 Z4 L10 Q65 5475 Z4 L10 Q66 5476 Z4 L10 Q67 5477 Z4 L10 Q68 5478 Z4 L10 Q69 5479 Z4 L10 Q70 5480 Z4 L10 Q71 5481 Z4 L10 Q72 5482 Z4 L10 Q73 5483 Z4 L10 Q74 5484 Z4 L10 Q75 5485 Z4 L10 Q76 5486 Z4 L10 Q77 5487 Z4 L10 Q78 5488 Z4 L10 Q79 5489 Z4 L10 Q80 5490 Z4 L10 Q81 5491 Z4 L10 Q82 5492 Z4 L10 Q83 5493 Z4 L10 Q84 5494 Z4 L10 Q85 5495 Z4 L10 Q86 5496 Z4 L10 Q87 5497 Z4 L10 Q88 5498 Z4 L10 Q89 5499 Z4 L10 Q90 5500 Z4 L10 Q91 5501 Z4 L10 Q92 5502 Z4 L10 Q93 5503 Z4 L10 Q94 5504 Z4 L10 Q95 5505 Z4 L10 Q96 5506 Z4 L10 Q97 5507 Z4 L10 Q98 5508 Z4 L10 Q99 5509 Z4 L10 Q100 5510 Z4 L10 Q101 5511 Z4 L10 Q102 5512 Z4 L10 Q103 5513 Z4 L11 Q40 5514 Z4 L11 Q41 5515 Z4 L11 Q42 5516 Z4 L11 Q43 5517 Z4 L11 Q44 5518 Z4 L11 Q45 5519 Z4 L11 Q46 5520 Z4 L11 Q47 5521 Z4 L11 Q48 5522 Z4 L11 Q49 5523 Z4 L11 Q50 5524 Z4 L11 Q51 5525 Z4 L11 Q52 5526 Z4 L11 Q53 5527 Z4 L11 Q54 5528 Z4 L11 Q55 5529 Z4 L11 Q56 5530 Z4 L11 Q57 5531 Z4 L11 Q58 5532 Z4 L11 Q59 5533 Z4 L11 Q60 5534 Z4 L11 Q61 5535 Z4 L11 Q62 5536 Z4 L11 Q63 5537 Z4 L11 Q64 5538 Z4 L11 Q65 5539 Z4 L11 Q66 5540 Z4 L11 Q67 5541 Z4 L11 Q68 5542 Z4 L11 Q69 5543 Z4 L11 Q70 5544 Z4 L11 Q71 5545 Z4 L11 Q72 5546 Z4 L11 Q73 5547 Z4 L11 Q74 5548 Z4 L11 Q75 5549 Z4 L11 Q76 5550 Z4 L11 Q77 5551 Z4 L11 Q78 5552 Z4 L11 Q79 5553 Z4 L11 Q80 5554 Z4 L11 Q81 5555 Z4 L11 Q82 5556 Z4 L11 Q83 5557 Z4 L11 Q84 5558 Z4 L11 Q85 5559 Z4 L11 Q86 5560 Z4 L11 Q87 5561 Z4 L11 Q88 5562 Z4 L11 Q89 5563 Z4 L11 Q90 5564 Z4 L11 Q91 5565 Z4 L11 Q92 5566 Z4 L11 Q93 5567 Z4 L11 Q94 5568 Z4 L11 Q95 5569 Z4 L11 Q96 5570 Z4 L11 Q97 5571 Z4 L11 Q98 5572 Z4 L11 Q99 5573 Z4 L11 Q100 5574 Z4 L11 Q101 5575 Z4 L11 Q102 5576 Z4 L12 Q40 5577 Z4 L12 Q41 5578 Z4 L12 Q42 5579 Z4 L12 Q43 5580 Z4 L12 Q44 5581 Z4 L12 Q45 5582 Z4 L12 Q46 5583 Z4 L12 Q47 5584 Z4 L12 Q48 5585 Z4 L12 Q49 5586 Z4 L12 Q50 5587 Z4 L12 Q51 5588 Z4 L12 Q52 5589 Z4 L12 Q53 5590 Z4 L12 Q54 5591 Z4 L12 Q55 5592 Z4 L12 Q56 5593 Z4 L12 Q57 5594 Z4 L12 Q58 5595 Z4 L12 Q59 5596 Z4 L12 Q60 5597 Z4 L12 Q61 5598 Z4 L12 Q62 5599 Z4 L12 Q63 5600 Z4 L12 Q64

TABLE 1-34 5601 Z4 L12 Q64 5602 Z4 L12 Q65 5603 Z4 L12 Q66 5604 Z4 L12 Q67 5605 Z4 L12 Q68 5606 Z4 L12 Q69 5607 Z4 L12 Q70 5608 Z4 L12 Q71 5609 Z4 L12 Q72 5610 Z4 L12 Q73 5611 Z4 L12 Q74 5612 Z4 L12 Q75 5613 Z4 L12 Q76 5614 Z4 L12 Q77 5615 Z4 L12 Q78 5616 Z4 L12 Q79 5617 Z4 L12 Q80 5618 Z4 L12 Q81 5619 Z4 L12 Q82 5620 Z4 L12 Q83 5621 Z4 L12 Q84 5622 Z4 L12 Q85 5623 Z4 L12 Q86 5624 Z4 L12 Q87 5625 Z4 L12 Q88 5626 Z4 L12 Q89 5627 Z4 L12 Q90 5628 Z4 L12 Q91 5629 Z4 L12 Q92 5630 Z4 L12 Q93 5631 Z4 L12 Q94 5632 Z4 L12 Q95 5633 Z4 L12 Q96 5634 Z4 L12 Q97 5635 Z4 L12 Q98 5636 Z4 L12 Q99 5637 Z4 L12 Q100 5638 Z4 L12 Q101 5639 Z4 L12 Q102 5640 Z4 L12 Q103 5641 Z4 L13 Q40 5642 74 L13 Q41 5643 Z4 L13 Q42 5644 Z4 L13 Q43 5645 Z4 L13 Q44 5646 Z4 L13 Q45 5647 Z4 L13 Q46 5648 Z4 L13 Q47 5649 Z4 L13 Q48 5650 Z4 L13 Q49 5651 Z4 L13 Q50 5652 Z4 L13 Q51 5653 Z4 L13 Q52 5654 Z4 L13 Q53 5655 Z4 L13 Q54 5656 Z4 L13 Q55 5657 Z4 L13 Q56 5658 Z4 L13 Q57 5659 Z4 L13 Q58 5660 Z4 L13 Q59 5661 Z4 L13 Q60 5662 Z4 L13 Q61 5663 Z4 L13 Q62 5664 Z4 L13 Q63 5665 Z4 L13 Q64 5666 Z4 L13 Q65 5667 Z4 L13 Q66 5668 Z4 L13 Q67 5669 Z4 L13 Q68 5670 Z4 L13 Q69 5674 Z4 L13 Q70 5672 Z4 L13 Q71 5673 Z4 L13 Q72 5674 Z4 L13 Q73 5675 Z4 L13 Q74 5676 Z4 L13 Q75 5677 Z4 L13 Q76 5678 Z4 L13 Q77 5679 Z4 L13 Q78 5680 Z4 L13 Q79 5681 Z4 L13 Q80 5682 Z4 L13 Q81 5683 Z4 L13 Q82 5684 Z4 L13 Q83 5685 Z4 L13 Q84 5686 Z4 L13 Q85 5687 Z4 L13 Q86 5688 Z4 L13 Q87 5689 Z4 L13 Q88 5690 Z4 L13 Q89 5691 Z4 L13 Q90 5692 Z4 L13 Q91 5693 Z4 L13 Q92 5694 Z4 L13 Q93 5695 Z4 L13 Q94 5696 Z4 L13 Q95 5697 Z4 L13 Q96 5698 Z4 L13 Q97 5699 Z4 L13 Q98 5700 Z4 L13 Q99 5701 Z4 L13 Q100 5702 Z4 L13 Q101 5703 Z4 L13 Q102 5704 Z4 L13 Q103 5705 Z4 L14 Q40 5706 Z4 L14 Q41 5707 Z4 L14 Q42 5708 Z4 L14 Q43 5709 Z4 L14 Q44 5710 Z4 L14 Q45 5711 Z4 L14 Q46 5712 Z4 L14 Q47 5713 Z4 L14 Q48 5714 Z4 L14 Q49 5715 Z4 L14 Q50 5716 Z4 L14 Q51 5717 Z4 L14 Q52 5718 Z4 L14 Q53 5719 Z4 L14 Q54 5720 Z4 L14 Q55 5721 Z4 L14 Q56 5722 Z4 L14 Q57 5723 Z4 L14 Q58 5724 Z4 L14 Q59 5725 Z4 L14 Q60 5726 Z4 L14 Q61 5727 Z4 L14 Q62 5728 Z4 L14 Q63 5729 Z4 L14 Q64 5730 Z4 L14 Q65 5731 Z4 L14 Q66 5732 Z4 L14 Q67 5733 Z4 L14 Q68 5734 Z4 L14 Q69 5735 Z4 L14 Q70 5736 Z4 L14 Q71 5737 Z4 L14 Q72 5738 Z4 L14 Q73 5739 Z4 L14 Q74 5740 Z4 L14 Q75 5741 Z4 L14 Q76 5742 Z4 L14 Q77 5743 Z4 L14 Q78 5744 Z4 L14 Q79 5745 Z4 L14 Q80 5746 Z4 L14 Q81 5747 Z4 L14 Q82 5748 Z4 L14 Q83 5749 Z4 L14 Q84 5750 Z4 L14 Q85 5751 Z4 L14 Q86 5752 Z4 L14 Q87 5753 Z4 L14 Q88 5754 Z4 L14 Q89 5755 Z4 L14 Q90 5756 Z4 L14 Q91 5757 Z4 L14 Q92 5758 Z4 L14 Q93 5759 Z4 L14 Q94 5760 Z4 L14 Q95 5761 Z4 L14 Q96 5762 Z4 L14 Q97 5763 Z4 L14 Q98 5764 Z4 L14 Q99 5765 Z4 L14 Q100 5766 Z4 L14 Q101 5767 Z4 L14 Q102 5768 Z4 L14 Q103 5769 Z1 L15 Q1 5770 Z1 L15 Q2 5771 Z1 L15 Q3 5772 Z1 L15 Q4 5773 Z1 L15 Q5 5774 Z1 L15 Q6 5775 Z1 L15 Q7 5776 Z1 L15 Q8 5777 Z1 L15 Q9 5778 Z1 L15 Q10 5779 Z1 L15 Q11 5780 Z1 L15 Q12 5781 Z1 L15 Q13 5782 Z1 L15 Q14 5783 Z1 L15 Q15 5784 Z1 L15 Q16 5785 Z1 L15 Q17 5786 Z1 L15 Q18 5787 Z1 L15 Q19 5788 Z1 L15 Q20 5789 Z1 L15 Q21 5790 Z1 L15 Q22 5791 Z1 L15 Q23 5792 Z1 L15 Q24 5793 Z1 L15 Q25 5794 Z1 L15 Q26 5795 Z1 L15 Q27 5796 Z1 L15 Q28 5797 Z1 L15 Q29 5798 Z1 L15 Q30 5799 Z1 L15 Q31 5800 Z1 L15 Q32 5801 Z1 L15 Q33

TABLE 1-35 5802 Z1 L15 Q34 5803 Z1 L15 Q35 5804 Z1 L15 Q36 5805 Z1 L15 Q37 5806 Z1 L15 Q38 5807 Z1 L15 Q39 5808 Z1 L15 Q40 5809 Z1 L15 Q41 5810 Z1 L15 Q42 5811 Z1 L15 Q43 5812 Z1 L15 Q44 5813 Z1 L15 Q45 5814 Z1 L15 Q46 5815 Z1 L15 Q47 5816 Z1 L15 Q48 5817 Z1 L15 Q49 5818 Z1 L15 Q50 5819 Z1 L15 Q51 5820 Z1 L15 Q52 5821 Z1 L15 Q53 5822 Z1 L15 Q54 5823 Z1 L15 Q55 5824 Z1 L15 Q56 5825 Z1 L15 Q57 5826 Z1 L15 Q58 5827 Z1 L15 Q59 5828 Z1 L15 Q60 5829 Z1 L15 Q61 5830 Z1 L15 Q62 5831 Z1 L15 Q63 5832 Z1 L15 Q64 5833 Z1 L15 Q65 5834 Z1 L15 Q66 5835 Z1 L15 Q67 5836 Z1 L15 Q68 5837 Z1 L15 Q69 5838 Z1 L15 Q70 5839 Z1 L15 Q71 5840 Z1 L15 Q72 5841 Z1 L15 Q73 5842 Z1 L15 Q74 5843 Z1 L15 Q75 5844 Z1 L15 Q76 5845 Z1 L15 Q77 5846 Z1 L15 Q78 5847 Z1 L15 Q79 5848 Z1 L15 Q80 5849 Z1 L15 Q81 5850 Z1 L15 Q82 5851 Z1 L15 Q83 5852 Z1 L15 Q84 5853 Z1 L15 Q85 5854 Z1 L15 Q86 5855 Z1 L15 Q87 5856 Z1 L15 Q88 5857 Z1 L15 Q89 5858 Z1 L15 Q90 5859 Z1 L15 Q91 5860 Z1 L15 Q92 5861 Z1 L15 Q93 5862 Z1 L15 Q94 5863 Z1 L15 Q95 5864 Z1 L15 Q96 5865 Z1 L15 Q97 5866 Z1 L15 Q98 5867 Z1 L15 Q99 5868 Z1 L15 Q100 5869 Z1 L15 Q101 5870 Z1 L15 Q102 5871 Z1 L15 Q103 5872 Z1 L16 Q1 5873 Z1 L16 Q2 5874 Z1 L16 Q3 5875 Z1 L16 Q4 5876 Z1 L16 Q5 5877 Z1 L16 Q6 5878 Z1 L16 Q7 5879 Z1 L16 Q8 5880 Z1 L16 Q9 5881 Z1 L16 Q10 5882 Z1 L16 Q11 5883 Z1 L16 Q12 5884 Z1 L16 Q13 5885 Z1 L16 Q14 5886 Z1 L16 Q15 5887 Z1 L16 Q16 5888 Z1 L16 Q17 5889 Z1 L16 Q18 5890 Z1 L16 Q19 5891 Z1 L16 Q20 5892 Z1 L16 Q21 5893 Z1 L16 Q22 5894 Z1 L16 Q23 5895 Z1 L16 Q24 5896 Z1 L16 Q25 5897 Z1 L16 Q26 5898 Z1 L16 Q27 5899 Z1 L16 Q28 5900 Z1 L16 Q29 5901 Z1 L16 Q30 5902 Z1 L16 Q31 5903 Z1 L16 Q32 5904 Z1 L16 Q33 5905 Z1 L16 Q34 5906 Z1 L16 Q35 5907 Z1 L16 Q36 5908 Z1 L16 Q37 5909 Z1 L16 Q38 5910 Z1 L16 Q39 5911 Z1 L16 Q40 5912 Z1 L16 Q41 5913 Z1 L16 Q42 5914 Z1 L16 Q43 5915 Z1 L16 Q44 5916 Z1 L16 Q45 5917 Z1 L16 Q46 5918 Z1 L16 Q47 5919 Z1 L16 Q48 5920 Z1 L16 Q49 5921 Z1 L16 Q50 5922 Z1 L16 Q51 5923 Z1 L16 Q52 5924 Z1 L16 Q53 5925 Z1 L16 Q54 5926 Z1 L16 Q55 5927 Z1 L16 Q56 5928 Z1 L16 Q57 5929 Z1 L16 Q58 5930 Z1 L16 Q59 5931 Z1 L16 Q60 5932 Z1 L16 Q61 5933 Z1 L16 Q62 5934 Z1 L16 Q63 5935 Z1 L16 Q64 5936 Z1 L16 Q65 5937 Z1 L16 Q66 5938 Z1 L16 Q67 5939 Z1 L16 Q68 5940 Z1 L16 Q69 5941 Z1 L16 Q70 5942 Z1 L16 Q71 5943 Z1 L16 Q72 5944 Z1 L16 Q73 5945 Z1 L16 Q74 5946 Z1 L16 Q75 5947 Z1 L16 Q76 5948 Z1 L16 Q77 5949 Z1 L16 Q78 5950 Z1 L16 Q79 5951 Z1 L16 Q80 5952 Z1 L16 Q81 5953 Z1 LI 6 Q82 5954 Z1 L16 Q83 5955 Z1 L16 Q84 5956 Z1 L16 Q85 5957 Z1 L16 Q86 5958 Z1 L16 Q87 5959 Z1 L16 Q88 5960 Z1 L16 Q89 5961 Z1 L16 Q90 5962 Z1 L16 Q91 5963 Z1 L16 Q92 5964 Z1 L16 Q93 5965 Z1 L16 Q94 5960 Z1 L16 Q95 5967 Z1 L16 Q96 5968 Z1 L16 Q97 5969 Z1 L16 Q98 5970 Z1 L16 Q99 5971 Z1 L16 Q100 5972 Z1 L16 Q101 5973 Z1 L16 Q102 5974 Z1 L16 Q103 5975 Z1 L17 Q1 5976 Z1 L17 Q2 5977 Z1 L17 Q3 5978 Z1 L17 Q4 5979 Z1 L17 Q5 5980 Z1 L17 Q6 5981 Z1 L17 Q7 5982 Z1 L17 Q8 5983 Z1 L17 Q9 5984 Z1 L17 Q10 5985 Z1 L17 Q11 5986 Z1 L17 Q12 5987 Z1 L17 Q13 5988 Z1 L17 Q14 5989 Z1 L17 Q15 5990 Z1 L17 Q16 5991 Z1 L17 Q17 5992 Z1 L17 Q18 5993 Z1 L17 Q19 5994 Z1 L17 Q20 5995 Z1 L17 Q21 5996 Z1 L17 Q22 5997 Z1 L17 Q23 5998 Z1 L17 Q24 5999 Z1 L17 Q25 5600 Z1 L17 Q26 5601 Z1 L17 Q27 5602 Z1 L17 Q28

TABLE 1-36 6003 Z1 L17 Q29 6004 Z1 L17 Q30 6005 Z1 L17 Q31 6006 Z1 L17 Q32 6007 Z1 L17 Q33 6008 Z1 L17 Q34 6009 Z1 L17 Q35 6010 Z1 L17 Q36 6011 Z1 L17 Q37 6012 Z1 L17 Q38 6013 Z1 L17 Q39 6014 Z1 L17 Q40 6015 Z1 L17 Q41 6016 Z1 L17 Q42 6017 Z1 L17 Q43 6018 Z1 L17 Q44 6019 Z1 L17 Q45 6020 Z1 L17 Q46 6021 Z1 L17 Q47 6022 Z1 L17 Q48 6023 Z1 L17 Q49 6024 Z1 L17 Q50 6025 Z1 L17 Q51 6026 Z1 L17 Q52 6027 Z1 L17 Q53 6028 Z1 L17 Q54 6029 Z1 L17 Q55 6030 Z1 L17 Q56 6031 Z1 L17 Q57 6032 Z1 L17 Q58 6033 Z1 L17 Q59 6034 Z1 L17 Q60 6035 Z1 L17 Q61 6036 Z1 L17 Q62 6037 Z1 L17 Q63 6038 Z1 L17 Q64 6039 Z1 L17 Q65 6040 Z1 L17 Q66 6041 Z1 L17 Q67 6042 Z1 L17 Q68 6043 Z1 L17 Q69 6044 Z1 L17 Q70 6045 Z1 L17 Q71 6046 Z1 L17 Q72 6047 Z1 L17 Q73 6048 Z1 L17 Q74 6049 Z1 L17 Q75 6050 Z1 L17 Q76 6051 Z1 L17 Q77 6052 Z1 L17 Q78 6053 Z1 L17 Q79 6054 Z1 L17 Q80 6055 Z1 L17 Q81 6056 Z1 L17 Q82 6057 Z1 L17 Q83 6058 Z1 L17 Q84 6059 Z1 L17 Q85 6060 Z1 L17 Q86 6061 Z1 L17 Q87 6062 Z1 L17 Q88 6063 Z1 L17 Q89 6064 Z1 L17 Q90 6065 Z1 L17 Q91 6066 Z1 L17 Q92 6067 Z1 L17 Q93 6068 Z1 L17 Q94 6069 Z1 L17 Q95 6070 Z1 L17 Q96 6071 Z1 L17 Q97 6072 Z1 L17 Q98 6073 Z1 L17 Q99 6074 Z1 L17 Q100 6075 Z1 L17 Q101 6076 Z1 L17 Q102 6077 Z1 L17 Q103 6078 Z1 L18 Q1 6079 Z1 L18 Q2 6080 Z1 L18 Q3 6081 Z1 L18 Q4 6082 Z1 L18 Q5 6083 Z1 L18 Q6 6084 Z1 L18 Q7 6085 Z1 L18 Q8 6086 Z1 L18 Q9 6087 Z1 L18 Q10 6088 Z1 L18 Q11 6089 Z1 L18 Q12 6090 Z1 L18 Q13 6091 Z1 L18 Q14 6092 Z1 L18 Q15 6093 Z1 L18 Q16 6094 Z1 L18 Q17 6095 Z1 L18 Q18 6096 Z1 L18 Q19 6097 Z1 L18 Q20 6098 Z1 L18 Q21 6099 Z1 L18 Q22 6100 Z1 L18 Q23 6101 Z1 L18 Q24 6102 Z1 L18 Q25 6103 Z1 L18 Q26 6104 Z1 L18 Q27 6105 Z1 L18 Q28 6106 Z1 L18 Q29 6107 Z1 L18 Q30 6108 Z1 L18 Q31 6109 Z1 L18 Q32 6110 Z1 L18 Q33 6111 Z1 L18 Q34 6112 Z1 L18 Q35 6113 Z1 L18 Q36 6114 Z1 L18 Q37 6115 Z1 L18 Q38 6116 Z1 L18 Q39 6117 Z1 L18 Q40 6118 Z1 L18 Q41 6119 Z1 L18 Q42 6120 Z1 L18 Q43 6121 Z1 L18 Q44 6022 Z1 L18 Q45 6023 Z1 L18 Q46 6024 Z1 L18 Q47 6025 Z1 L18 Q48 6026 Z1 L18 Q49 6027 Z1 L18 Q50 6028 Z1 L18 Q51 6029 Z1 L18 Q52 6030 Z1 L18 Q53 6031 Z1 L18 Q54 6032 Z1 L18 Q55 6033 Z1 L18 Q56 6034 Z1 L18 Q57 6035 Z1 L18 Q58 6036 Z1 L18 Q59 6137 Z1 L18 Q60 6138 Z1 L18 Q61 6139 Z1 L18 Q62 6140 Z1 L18 Q63 6141 Z1 L18 Q64 6142 Z1 L18 Q65 6143 Z1 L18 Q66 6144 Z1 L18 Q67 6145 Z1 L18 Q68 6146 Z1 L18 Q69 6147 Z1 L18 Q70 6148 Z1 L18 Q71 6149 Z1 L18 Q72 6150 Z1 L18 Q73 6151 Z1 L18 Q74 6152 Z1 L18 Q75 6153 Z1 L18 Q76 6154 Z1 L18 Q77 6155 Z1 L18 Q78 6156 Z1 L18 Q79 6157 Z1 L18 Q80 6158 Z1 L18 Q81 6159 Z1 L18 Q82 6160 Z1 L18 Q83 6161 Z1 L18 Q84 6162 Z1 L18 Q85 6163 Z1 L18 Q86 6164 Z1 L18 Q87 6165 Z1 L18 Q88 6166 Z1 L18 Q89 6187 Z1 L18 Q90 6168 Z1 L18 Q91 6169 Z1 L18 Q92 6170 Z1 L18 Q93 6171 Z1 L18 Q94 6172 Z1 L18 Q95 6173 Z1 L18 Q96 6174 Z1 L18 Q97 6175 Z1 L18 Q98 6176 Z1 L18 Q99 6177 Z1 L18 Q100 6178 Z1 L18 Q101 6179 Z1 L18 Q102 6180 Z1 L18 Q103 6181 Z1 L19 Q1 6182 Z1 L19 Q2 6183 Z1 L19 Q3 6184 Z1 L19 Q4 6185 Z1 L19 Q5 6186 Z1 L19 Q6 6187 Z1 L19 Q7 6188 Z1 L19 Q8 6189 Z1 L19 Q9 6190 Z1 L19 Q10 6191 Z1 L19 Q11 6192 Z1 L19 Q12 6193 Z1 L19 Q13 6194 Z1 L19 Q14 6195 Z1 L19 Q15 6196 Z1 L19 Q16 6197 Z1 L19 Q17 6198 Z1 L19 Q18 6199 Z1 L19 Q19 6200 Z1 L19 Q20 6201 Z1 L19 Q21 6202 Z1 L19 Q22 6203 Z1 L19 Q23

TABLE 1-37 6204 Z1 L19 Q24 6205 Z1 L19 Q25 6206 Z1 L19 Q26 6207 Z1 L19 Q27 6208 Z1 L19 Q28 6209 Z1 L19 Q29 6210 Z1 L19 Q30 6211 Z1 L19 Q31 6212 Z1 L19 Q32 6213 Z1 L19 Q33 6214 Z1 L19 Q34 6215 Z1 L19 Q35 6216 Z1 L19 Q36 6217 Z1 L19 Q37 6218 Z1 L19 Q38 6219 Z1 L19 Q39 6220 Z1 L19 Q40 6221 Z1 L19 Q41 6222 Z1 L19 Q42 6223 Z1 L19 Q43 6224 Z1 L19 Q44 6225 Z1 L19 Q45 6226 Z1 L19 Q46 6227 Z1 L19 Q47 6228 Z1 L19 Q48 6229 Z1 L19 Q49 6230 Z1 L19 Q50 6231 Z1 L19 Q51 6232 Z1 L19 Q52 6233 Z1 L19 Q53 6234 Z1 L19 Q54 6235 Z1 L19 Q55 6236 Z1 L19 Q56 6237 Z1 L19 Q57 6238 Z1 L19 Q58 6239 Z1 L19 Q59 6240 Z1 L19 Q60 6241 Z1 L19 Q61 6242 Z1 L19 Q62 6243 Z1 L19 Q63 6244 Z1 L19 Q64 6245 Z1 L19 Q65 6246 Z1 L19 Q66 6247 Z1 L19 Q67 6248 Z1 L19 Q68 6249 Z1 L19 Q69 6250 Z1 L19 Q70 6251 Z1 L19 Q71 6252 Z1 L19 Q72 6253 Z1 L19 Q73 6254 Z1 L19 Q74 6255 Z1 L19 Q75 6256 Z1 L19 Q76 6257 Z1 L19 Q77 6258 Z1 L19 Q78 6259 Z1 L19 Q79 6260 Z1 L19 Q80 6261 Z1 L19 Q81 6262 Z1 L19 Q82 6263 Z1 L19 Q83 6264 Z1 L19 Q84 6265 Z1 L19 Q85 6266 Z1 L19 Q86 6267 Z1 L19 Q87 6268 Z1 L19 Q88 6269 Z1 L19 Q89 6270 Z1 L19 Q90 6271 Z1 L19 Q91 6272 Z1 L19 Q92 6273 Z1 L19 Q93 6274 Z1 L19 Q94 6275 Z1 L19 Q95 6276 Z1 L19 Q96 6277 Z1 L19 Q97 6278 Z1 L19 Q98 6279 Z1 L19 Q99 6280 Z1 L19 Q100 6281 Z1 L19 Q101 6282 Z1 L19 Q102 6283 Z1 L19 Q103 6284 Z1 L20 Q1 6285 Z1 L20 Q2 6286 Z1 L20 Q3 6287 Z1 L20 Q4 6288 Z1 L20 Q5 6289 Z1 L20 Q6 6290 Z1 L20 Q7 6291 Z1 L20 Q8 6292 Z1 L20 Q9 6293 Z1 L20 Q10 6294 Z1 L20 Q11 6295 Z1 L20 Q12 6296 Z1 L20 Q13 6297 Z1 L20 Q14 6298 Z1 L20 Q15 6299 Z1 L20 Q16 6300 Z1 L20 Q17 6301 Z1 L20 Q18 6302 Z1 L20 Q19 6303 Z1 L20 Q20 6304 Z1 L20 Q21 6305 Z1 L20 Q22 6306 Z1 L20 Q23 6307 Z1 L20 Q24 6308 Z1 L20 Q25 6309 Z1 L20 Q26 6310 Z1 L20 Q27 6311 Z1 L20 Q28 6312 Z1 L20 Q29 6313 Z1 L20 Q30 6314 Z1 L20 Q31 6315 Z1 L20 Q32 6316 Z1 L20 Q33 6317 Z1 L20 Q34 6318 Z1 L20 Q35 6319 Z1 L20 Q36 6320 Z1 L20 Q37 6321 Z1 L20 Q38 6322 Z1 L20 Q39 6323 Z1 L20 Q40 6324 Z1 L20 Q41 6325 Z1 L20 Q42 6326 Z1 L20 Q43 6327 Z1 L20 Q44 6328 Z1 L20 Q45 6329 Z1 L20 Q46 6330 Z1 L20 Q47 6331 Z1 L20 Q48 6332 Z1 L20 Q49 6333 Z1 L20 Q50 6334 Z1 L20 Q51 6335 Z1 L20 Q52 6336 Z1 L20 Q53 6337 Z1 L20 Q54 6336 Z1 L20 Q55 6339 Z1 L20 Q56 6340 Z1 L20 Q57 6341 Z1 L20 Q58 6342 Z1 L20 Q59 6343 Z1 L20 Q60 6344 Z1 L20 Q61 6345 Z1 L20 Q62 6346 Z1 L20 Q63 6347 Z1 L20 Q64 6348 Z1 L20 Q65 6349 Z1 L20 Q66 6350 Z1 L20 Q67 6351 Z1 L20 Q68 6352 Z1 L20 Q69 6353 Z1 L20 Q70 6354 Z1 L20 Q71 6355 Z1 L20 Q72 6356 Z1 L20 Q73 6357 Z1 L20 Q74 6358 Z1 L20 Q75 6359 Z1 L20 Q76 6360 Z1 L20 Q77 6361 Z1 L20 Q78 6362 Z1 L20 Q79 6363 Z1 L20 Q80 6364 Z1 120 Q81 6365 Z1 L20 Q82 6366 Z1 L20 Q83 6367 Z1 L20 Q84 6368 Z1 L20 Q85 6369 Z1 L20 Q86 6370 Z1 L20 Q87 6371 Z1 L20 Q88 6372 Z1 L20 Q89 6373 Z1 L20 Q90 6374 Z1 L20 Q91 6375 Z1 L20 Q92 6376 Z1 L20 Q93 6377 Z1 L20 Q94 6378 Z1 L20 Q95 6379 Z1 L20 Q96 6380 Z1 L20 Q97 6381 Z1 L20 Q98 6382 Z1 L20 Q99 6383 Z1 L20 Q100 6384 Z1 L20 Q101 6385 Z1 L20 Q102 6386 Z1 L20 Q103 6387 Z1 L21 Q1 6388 Z1 L21 Q2 6389 Z1 L21 Q3 6390 Z1 L21 Q4 6391 Z1 L21 Q5 6392 Z1 L21 Q6 6393 Z1 L21 Q7 6394 Z1 L21 Q8 6395 Z1 L21 Q9 6396 Z1 L21 Q10 6397 Z1 L21 Q11 6398 Z1 L21 Q12 6399 Z1 L21 Q13 6400 Z1 L21 Q14 6401 Z1 L21 Q15 6402 Z1 L21 Q16 6403 Z1 L21 Q17 6404 Z1 L21 Q18

TABLE 1-38 6405 Z1 L21 Q19 6406 Z1 L21 Q20 6407 Z1 L21 Q21 6408 Z1 L21 Q22 6409 Z1 L21 Q23 6410 Z1 L21 Q24 6411 Z1 L21 Q25 6412 Z1 L21 Q26 6413 Z1 L21 Q27 6414 Z1 L21 Q28 6415 Z1 L21 Q29 6416 Z1 L21 Q30 6417 Z1 L21 Q31 6418 Z1 L21 Q32 6419 Z1 L21 Q33 6420 Z1 L21 Q34 6421 Z1 L21 Q35 6422 Z1 L21 Q36 6423 Z1 L21 Q37 6424 Z1 L21 Q38 6425 Z1 L21 Q39 6426 Z1 L21 Q40 6427 Z1 L21 Q41 6428 Z1 L21 Q42 6429 Z1 L21 Q43 6430 Z1 L21 Q44 6431 Z1 L21 Q45 6432 Z1 L21 Q46 6433 Z1 L21 Q47 6434 Z1 L21 Q48 6435 Z1 L21 Q49 6436 Z1 L21 Q50 6437 Z1 L21 Q51 6438 Z1 L21 Q52 6439 Z1 L21 Q53 6440 Z1 L21 Q54 6441 Z1 L21 Q55 6442 Z1 L21 Q56 6443 Z1 L21 Q57 6444 Z1 L21 Q58 6445 Z1 L21 Q59 6446 Z1 L21 Q60 6447 Z1 L21 Q61 6448 Z1 L21 Q62 6449 Z1 L21 Q63 6450 Z1 L21 Q64 6451 Z1 L21 Q65 6452 Z1 L21 Q66 6453 Z1 L21 Q67 6454 Z1 L21 Q68 6455 Z1 L21 Q69 6456 Z1 L21 Q70 6457 Z1 L21 Q71 6458 Z1 L21 Q72 6459 Z1 L21 Q73 6460 Z1 L21 Q74 6461 Z1 L21 Q75 6462 Z1 L21 Q76 6463 Z1 L21 Q77 6464 Z1 L21 Q78 6465 Z1 L21 Q79 6466 Z1 L21 Q80 6467 Z1 L21 Q81 6468 Z1 L21 Q82 6469 Z1 L21 Q83 6470 Z1 L21 Q84 6471 Z1 L21 Q85 6472 Z1 L21 Q86 6473 Z1 L21 Q87 6474 Z1 L21 Q88 6475 Z1 L21 Q89 6476 Z1 L21 Q90 6477 Z1 L21 Q91 6478 Z1 L21 Q92 6479 Z1 L21 Q93 6480 Z1 L21 Q94 6481 Z1 L21 Q95 6482 Z1 L21 Q96 6483 Z1 L21 Q97 6484 Z1 L21 Q98 6485 Z1 L21 Q99 6486 Z1 L21 Q100 6487 Z1 L21 Q101 6488 Z1 L21 Q102 6489 Z1 L21 Q103 6490 Z1 L22 Q1 6491 Z1 L22 Q2 6492 Z1 L22 Q3 6493 Z1 L22 Q4 6494 Z1 L22 Q5 6495 Z1 L22 Q6 6496 Z1 L22 Q7 6497 Z1 L22 Q8 6498 Z1 L22 Q9 6499 Z1 L22 Q10 6500 Z1 L22 Q11 6501 Z1 L22 Q12 6502 Z1 L22 Q13 6503 Z1 L22 Q14 6504 Z1 L22 Q15 6505 Z1 L22 Q16 6506 Z1 L22 Q17 6507 Z1 L22 Q18 6508 Z1 L22 Q19 6509 Z1 L22 Q20 6510 Z1 L22 Q21 6511 Z1 L22 Q22 6512 Z1 L22 Q23 6513 Z1 L22 Q24 6514 Z1 L22 Q25 6515 Z1 L22 Q26 6516 Z1 L22 Q27 6517 Z1 L22 Q28 6518 Z1 L22 Q29 6519 Z1 L22 Q30 6520 Z1 L22 Q31 6521 Z1 L22 Q32 6522 Z1 L22 Q33 6523 Z1 L22 Q34 6524 Z1 L22 Q35 6525 Z1 L22 Q36 6526 Z1 L22 Q37 6527 Z1 L22 Q38 6528 Z1 L22 Q39 6529 Z1 L22 Q40 6530 Z1 L22 Q41 6531 Z1 L22 Q42 6532 Z1 L22 Q43 6533 Z1 L22 Q44 6534 Z1 L22 Q45 6535 Z1 L22 Q46 6536 Z1 L22 Q47 6537 Z1 L22 Q48 6538 Z1 L22 Q49 6539 Z1 L22 Q50 6540 Z1 L22 Q51 6541 Z1 L22 Q52 6542 Z1 L22 Q53 6543 Z1 L22 Q54 6544 Z1 L22 Q55 6545 Z1 L22 Q56 6546 Z1 L22 Q57 6547 Z1 L22 Q58 6548 Z1 L22 Q59 6549 Z1 L22 Q60 6550 Z1 L22 Q61 6551 Z1 L22 Q62 6552 Z1 L22 Q63 6553 Z1 L22 Q64 6554 Z1 L22 Q65 6555 Z1 L22 Q66 6556 Z1 L22 Q67 6557 Z1 L22 Q68 6558 Z1 L22 Q69 6559 Z1 L22 Q70 6560 Z1 L22 Q71 6561 Z1 L22 Q72 6562 Z1 L22 Q73 6563 Z1 L22 Q74 6564 Z1 L22 Q75 6565 Z1 L22 Q76 6566 Z1 L22 Q77 6567 Z1 L22 Q78 6568 Z1 L22 Q79 6569 Z1 L22 Q80 6570 Z1 L22 Q81 6571 Z1 L22 Q82 6572 Z1 L22 Q83 6573 Z1 L22 Q84 6574 Z1 L22 Q85 6575 Z1 L22 Q86 6576 Z1 L22 Q87 6577 Z1 L22 Q88 6578 Z1 L22 Q89 6579 Z1 L22 Q90 6580 Z1 L22 Q91 6581 Z1 L22 Q92 6582 Z1 L22 Q93 6583 Z1 L22 Q94 6584 Z1 L22 Q95 6585 Z1 L22 Q96 6586 Z1 L22 Q97 6587 Z1 L22 Q98 6588 Z1 L22 Q99 6589 Z1 L22 Q100 6590 Z1 L22 Q101 6591 Z1 L22 Q102 6592 Z1 L22 Q103 6593 Z1 L22 Q1 6594 Z1 L22 Q2 6595 Z1 L22 Q3 6596 Z1 L22 Q4 6597 Z1 L22 Q5 6598 Z1 L22 Q6 6599 Z1 L22 Q7 6600 Z1 L22 Q8 6601 Z1 L22 Q9 6602 Z1 L22 Q10 6603 Z1 L22 Q11 6604 Z1 L22 Q12 6605 Z1 L22 Q13

TABLE 1-39 6606 Z1 L23 Q14 6607 Z1 L23 Q15 6608 Z1 L23 Q16 6609 Z1 L23 Q17 6610 Z1 L23 Q18 6611 Z1 L23 Q19 6612 Z1 L23 Q20 6613 Z1 L23 Q21 6614 Z1 L23 Q22 6615 Z1 L23 Q23 6616 Z1 L23 Q24 6617 Z1 L23 Q25 6618 Z1 L23 Q26 6619 Z1 L23 Q27 6620 Z1 L23 Q28 6621 Z1 L23 Q29 6622 Z1 L23 Q30 6623 Z1 L23 Q31 6624 Z1 L23 Q32 6625 Z1 L23 Q33 6625 Z1 L23 Q34 6627 Z1 L23 Q35 6628 Z1 L23 Q36 6629 Z1 L23 Q37 6630 Z1 L23 Q38 6631 Z1 L23 Q39 6632 Z1 L23 Q40 6633 Z1 L23 Q41 6634 Z1 L23 Q42 6635 Z1 L23 Q43 6636 Z1 L23 Q44 6637 Z1 L23 Q45 6638 Z1 L23 Q46 6639 Z1 L23 Q47 6640 Z1 L23 Q48 6641 Z1 L23 Q49 6642 Z1 L23 Q50 6643 Z1 L23 Q51 6644 Z1 L23 Q52 6645 Z1 L23 Q53 6646 Z1 L23 Q54 6647 Z1 L23 Q55 6648 Z1 L23 Q56 6649 Z1 L23 Q57 6650 Z1 L23 Q58 6651 Z1 L23 Q59 6652 Z1 L23 Q60 6653 Z1 L23 Q61 6654 Z1 L23 Q62 6655 Z1 L23 Q63 6656 Z1 L23 Q64 6657 Z1 L23 Q65 6658 Z1 L23 Q66 6659 Z1 L23 Q67 6660 Z1 L23 Q68 6661 Z1 L23 Q69 6662 Z1 L23 Q70 6663 Z1 L23 Q71 6664 Z1 L23 Q72 6665 Z1 L23 Q73 6666 Z1 L23 Q74 6667 Z1 L23 Q75 6668 Z1 L23 Q76 6669 Z1 L23 Q77 6670 Z1 L23 Q78 6671 Z1 L23 Q79 6672 Z1 L23 Q80 6673 Z1 L23 Q81 6674 Z1 L23 Q82 6675 Z1 L23 Q83 6676 Z1 L23 Q84 6677 Z1 L23 Q85 6678 Z1 L23 Q86 6679 Z1 L23 Q87 6680 Z1 L23 Q88 6681 Z1 L23 Q89 6682 Z1 L23 Q90 6683 Z1 L23 Q91 6684 Z1 L23 Q92 6685 Z1 L23 Q93 6686 Z1 L23 Q94 6687 Z1 L23 Q95 6688 Z1 L23 Q96 6689 Z1 L23 Q97 6690 Z1 L23 Q98 6691 Z1 L23 Q99 6692 Z1 L23 Q100 6693 Z1 L23 Q101 6694 Z1 L23 Q102 6695 Z1 L23 Q103 6696 Z1 L24 Q1 6697 Z1 L24 Q2 6698 Z1 L24 Q3 6699 Z1 L24 Q4 6700 Z1 L24 Q5 6701 Z1 L24 Q6 6702 Z1 L24 Q7 6703 Z1 L24 Q8 6704 Z1 L24 Q9 6705 Z1 L24 Q10 6706 Z1 L24 Q11 6707 Z1 L24 Q12 6708 Z1 L24 Q13 6709 Z1 L24 Q14 6710 Z1 L24 Q15 6711 Z1 L24 Q16 6712 Z1 L24 Q17 6713 Z1 L24 Q18 6714 Z1 L24 Q19 6715 Z1 L24 Q20 6716 Z1 L24 Q21 6717 Z1 L24 Q22 6718 Z1 L24 Q23 6719 Z1 L24 Q24 6720 Z1 L24 Q25 6721 Z1 L24 Q26 6722 Z1 L24 Q27 6723 Z1 L24 Q28 6724 Z1 L24 Q29 6725 Z1 L24 Q30 6726 Z1 L24 Q31 6727 Z1 L24 Q32 6728 Z1 L24 Q33 6729 Z1 L24 Q34 6730 Z1 L24 Q35 6731 Z1 L24 Q36 6732 Z1 L24 Q37 6733 Z1 L24 Q38 6734 Z1 L24 Q39 6735 Z1 L24 Q40 6736 Z1 L24 Q41 6737 Z1 L24 Q42 6738 Z1 L24 Q43 6739 Z1 L24 Q44 6740 Z1 L24 Q45 6741 Z1 L24 Q46 6742 Z1 L24 Q47 6743 Z1 L24 Q48 6744 Z1 L24 Q49 6745 Z1 L24 Q50 6746 Z1 L24 Q51 6747 Z1 L24 Q52 6748 Z1 L24 Q53 6749 Z1 L24 Q54 6750 Z1 L24 Q55 6751 Z1 L24 Q56 6752 Z1 L24 Q57 6753 Z1 L24 Q58 6754 Z1 L24 Q59 6755 Z1 L24 Q60 6756 Z1 L24 Q61 6757 Z1 L24 Q62 6758 Z1 L24 Q63 6759 Z1 L24 Q64 6760 Z1 L24 Q65 6761 Z1 L24 Q66 6762 Z1 L24 Q67 6763 Z1 L24 Q68 6764 Z1 L24 Q69 6765 Z1 L24 Q70 6766 Z1 L24 Q71 5767 Z1 L24 Q72 6768 Z1 L24 Q73 6769 Z1 L24 Q74 6770 Z1 L24 Q75 6771 Z1 L24 Q76 6772 Z1 L24 Q77 6773 Z1 L24 Q78 6774 Z1 L24 Q79 6775 Z1 L24 Q80 6776 Z1 L24 Q81 6777 Z1 L24 Q82 6778 Z1 L24 Q83 6779 Z1 L24 Q84 6780 Z1 L24 Q85 6781 Z1 L24 Q86 6782 Z1 L24 Q87 6783 Z1 L24 Q88 6784 Z1 L24 Q89 6785 Z1 L24 Q90 6786 Z1 L24 Q91 6787 Z1 L24 Q92 6788 Z1 L24 Q93 6789 Z1 L24 Q94 6790 Z1 L24 Q95 6791 Z1 L24 Q96 6792 Z1 L24 Q97 6793 Z1 L24 Q98 6794 Z1 L24 Q99 6795 Z1 L24 Q100 6796 Z1 L24 Q101 6797 Z1 L24 Q102 6798 Z1 L24 Q103 6799 Z1 L25 Q1 6800 Z1 L25 Q2 6801 Z1 L25 Q3 6802 Z1 L25 Q4 6803 Z1 L25 Q5 6804 Z1 L25 Q6 6805 Z1 L25 Q7 6806 Z1 L25 Q8

TABLE 1-40 6807 Z1 L25 Q9 6808 Z1 L25 Q10 6809 Z1 L25 Q11 6810 Z1 L25 Q12 6811 Z1 L25 Q13 6812 Z1 L25 Q14 6813 Z1 L25 Q15 6814 Z1 L25 Q16 6815 Z1 L25 Q17 6816 Z1 L25 Q18 6817 Z1 L25 Q19 6818 Z1 L25 Q20 6319 Z1 L25 Q21 6820 Z1 L25 Q22 6321 Z1 L25 Q23 6822 Z1 L25 Q24 6323 Z1 L25 Q25 6324 Z1 L25 Q26 6825 Z1 L25 Q27 6826 Z1 L25 Q28 6827 Z1 L25 Q29 6828 Z1 L25 Q30 6829 Z1 L25 Q31 6830 Z1 L25 Q32 6834 Z1 L25 Q33 6832 Z1 L25 Q34 6833 Z1 L25 Q35 6834 Z1 L25 Q36 6835 Z1 L25 Q37 6836 Z1 L25 Q38 6837 Z1 L25 Q39 6838 Z1 L25 Q40 6839 Z1 L25 Q41 6340 Z1 L25 Q42 6841 Z1 L25 Q43 6842 Z1 L25 Q44 6343 Z1 L25 Q45 6844 Z1 L25 Q46 6845 Z1 L25 Q47 6846 Z1 L25 Q48 6847 Z1 L25 Q49 6848 Z1 L25 Q50 6849 Z1 L25 Q51 6850 Z1 L25 Q52 6851 Z1 L25 Q53 6852 Z1 L25 Q54 6853 Z1 L25 Q55 6854 Z1 L25 Q56 6855 Z1 L25 Q57 6856 Z1 L25 Q58 6857 Z1 L25 Q59 6858 Z1 L25 Q60 6859 Z1 L25 Q61 6860 Z1 L25 Q62 6861 Z1 L25 Q63 6862 Z1 L25 Q64 6863 Z1 L25 Q65 6864 Z1 L25 Q66 6865 Z1 L25 Q67 6866 Z1 L25 Q68 6867 Z1 L25 Q69 6868 Z1 L25 Q70 6869 Z1 L25 Q71 6870 Z1 L25 Q72 6871 Z1 L25 Q73 6872 Z1 L25 Q74 6873 Z1 L25 Q75 6874 Z1 L25 Q76 6875 Z1 L25 Q77 6876 Z1 L25 Q78 6877 Z1 L25 Q79 6878 Z1 L25 Q80 6879 Z1 L25 Q81 6880 Z1 L25 Q82 6881 Z1 L25 Q83 6882 Z1 L25 Q84 6883 Z1 L25 Q85 6884 Z1 L25 Q86 6885 Z1 L25 Q87 6886 Z1 L25 Q88 6887 Z1 L25 Q89 6888 Z1 L25 Q90 6889 Z1 L25 Q91 6890 Z1 L25 Q92 6891 Z1 L25 Q93 6892 Z1 L25 Q94 6893 Z1 L25 Q95 6894 Z1 L25 Q96 6895 Z1 L25 Q97 6896 Z1 L25 Q98 6897 Z1 L25 Q99 6898 Z1 L25 Q100 6899 Z1 L25 Q101 6900 Z1 L25 Q102 6901 Z1 L25 Q103 6902 Z1 L26 Q1 6903 Z1 L26 Q2 6904 Z1 L26 Q3 6905 Z1 L26 Q4 6906 Z1 L26 Q5 6907 Z1 L26 Q6 6908 Z1 L26 Q7 6909 Z1 L26 Q8 6910 Z1 L26 Q9 6911 Z1 L26 Q10 6912 Z1 L26 Q11 6913 Z1 L26 Q12 6914 Z1 L26 Q13 6915 Z1 L26 Q14 6916 Z1 L26 Q15 6917 Z1 L26 Q16 6918 Z1 L26 Q17 6919 Z1 L26 Q18 6920 Z1 L26 Q19 6921 Z1 L26 Q20 6922 Z1 L26 Q21 6923 Z1 L26 Q22 6924 Z1 L26 Q23 6925 Z1 L26 Q24 6926 Z1 L26 Q25 6927 Z1 L26 Q26 6928 Z1 L26 Q27 6929 Z1 L26 Q28 6930 Z1 L26 Q29 6931 Z1 L26 Q30 6932 Z1 L26 Q31 6933 Z1 L26 Q32 6934 Z1 L26 Q33 6935 Z1 L26 Q34 6936 Z1 L26 Q35 6937 Z1 L26 Q36 6938 Z1 L26 Q37 6939 Z1 L26 Q38 6940 Z1 L26 Q39 6941 Z1 L26 Q40 6942 Z1 L26 Q41 6943 Z1 L26 Q42 6944 Z1 L26 Q43 6945 Z1 L26 Q44 6946 Z1 L26 Q45 6947 Z1 L26 Q46 6948 Z1 L26 Q47 6949 Z1 L26 Q48 6950 Z1 L26 Q49 6951 Z1 L26 Q50 6952 Z1 L26 Q51 6953 Z1 L26 Q52 6954 Z1 L26 Q53 6955 Z1 L26 Q54 5956 Z1 L26 Q55 6957 Z1 L26 Q56 6958 Z1 L26 Q57 6959 Z1 L26 Q58 6960 Z1 L26 Q59 6961 Z1 L26 Q60 6962 Z1 L26 Q61 6963 Z1 L26 Q62 6964 Z1 L26 Q63 6965 Z1 L26 Q64 6966 Z1 L26 Q65 6967 Z1 L26 Q66 6968 Z1 L26 Q67 6969 Z1 L26 Q68 6970 Z1 L26 Q69 6971 Z1 L26 Q70 6972 Z1 L26 Q71 6973 Z1 L26 Q72 6974 Z1 L26 Q73 6975 Z1 L26 Q74 6975 Z1 L26 Q75 6977 Z1 L25 Q76 6978 Z1 L26 Q77 6979 Z1 L26 Q78 6980 Z1 L26 Q79 6981 Z1 L26 Q80 6982 Z1 L26 Q81 6983 Z1 L26 Q82 6984 Z1 L26 Q83 6985 Z1 L26 Q84 6986 Z1 L26 Q85 6987 Z1 L26 Q86 6988 Z1 L26 Q87 6989 Z1 L26 Q88 6990 Z1 L26 Q89 6991 Z1 L26 Q90 6992 Z1 L26 Q91 6993 Z1 L26 Q92 6994 Z1 L26 Q93 6995 Z1 L26 Q94 6996 Z1 L26 Q95 6997 Z1 L26 Q96 6998 Z1 L26 Q97 6999 Z1 L26 Q98 7000 Z1 L26 Q99 7001 Z1 L26 Q100 7002 Z1 L26 Q101 7003 Z1 L26 Q102 7004 Z1 L26 Q103 7005 Z1 L27 Q1 7006 Z1 L27 Q2 7007 Z1 L27 Q3

TABLE 1-41 7008 Z1 L27 Q4 7009 Z1 L27 Q5 7010 Z1 L27 Q6 7011 Z1 L27 Q7 7012 Z1 L27 Q8 7013 Z1 L27 Q9 7014 Z1 L27 Q10 7015 Z1 L27 Q11 7016 Z1 L27 Q12 7017 Z1 L27 Q13 7018 Z1 L27 Q14 7019 Z1 L27 Q15 7020 Z1 L27 Q16 7021 Z1 L27 Q17 7022 Z1 L27 Q18 7023 Z1 L27 Q19 7024 Z1 L27 Q20 7025 Z1 L27 Q21 7026 Z1 L27 Q22 7027 Z1 L27 Q23 7028 Z1 L27 Q24 7029 Z1 L27 Q25 7030 Z1 L27 Q26 7031 Z1 L27 Q27 7032 Z1 L27 Q28 7033 Z1 L27 Q29 7034 Z1 L27 Q30 7035 Z1 L27 Q31 7036 Z1 L27 Q32 7037 Z1 L27 Q33 7038 Z1 L27 Q34 7039 Z1 L27 Q35 7040 Z1 L27 Q36 7041 Z1 L27 Q37 7042 Z1 L27 Q38 7043 Z1 L27 Q39 7044 Z1 L27 Q40 7045 Z1 L27 Q41 7046 Z1 L27 Q42 7047 Z1 L27 Q43 7048 Z1 L27 Q44 7049 Z1 L27 Q45 7050 Z1 L27 Q46 7051 Z1 L27 Q47 7052 Z1 L27 Q48 7053 Z1 L27 Q49 7054 Z1 L27 Q50 7055 Z1 L27 Q51 7056 Z1 L27 Q52 7057 Z1 L27 Q53 7058 Z1 L27 Q54 7059 Z1 L27 Q55 7060 Z1 L27 Q56 7061 Z1 L27 Q57 7062 Z1 L27 Q58 7063 Z1 L27 Q59 7064 Z1 L27 Q60 7065 Z1 L27 Q61 7066 Z1 L27 Q62 7067 Z1 L27 Q63 7068 Z1 L27 Q64 7069 Z1 L27 Q65 7070 Z1 L27 Q66 7071 Z1 L27 Q67 7072 Z1 L27 Q68 7073 Z1 L27 Q69 7074 Z1 L27 Q70 7075 Z1 L27 Q71 7076 Z1 L27 Q72 7077 Z1 L27 Q73 7078 Z1 L27 Q74 7079 Z1 L27 Q75 7080 Z1 L27 Q76 7081 Z1 L27 Q77 7082 Z1 L27 Q78 7083 Z1 L27 Q79 7084 Z1 L27 Q80 7085 Z1 L27 Q81 7086 Z1 L27 Q82 7087 Z1 L27 Q83 7088 Z1 L27 Q84 7089 Z1 L27 Q85 7090 Z1 L27 Q86 7091 Z1 L27 Q87 7092 Z1 L27 Q88 7093 Z1 L27 Q89 7094 Z1 L27 Q90 7095 Z1 L27 Q91 7096 Z1 L27 Q92 7097 Z1 L27 Q93 7098 Z1 L27 Q94 7099 Z1 L27 Q95 7100 Z1 L27 Q96 7101 Z1 L27 Q97 7402 Z1 L27 Q98 7103 Z1 L27 Q99 7104 Z1 L27 Q100 7105 Z1 L27 Q101 7106 Z1 L27 Q102 7407 Z1 L27 Q103 7108 Z1 L28 Q1 7109 Z1 L28 Q2 7110 Z1 L28 Q3 7111 Z1 L28 Q4 7112 Z1 L28 Q5 7113 Z1 L28 Q6 7114 Z1 L28 Q7 7115 Z1 L28 Q8 7116 Z1 L28 Q9 7117 Z1 L28 Q10 7718 Z1 L28 Q11 7719 Z1 L28 Q12 7120 Z1 L28 Q13 7121 Z1 L28 Q14 7122 Z1 L28 Q15 7123 Z1 L28 Q16 7124 Z1 L28 Q17 7125 Z1 L28 Q18 7126 Z1 L28 Q19 7127 Z1 L28 Q20 7128 Z1 L28 Q21 7129 Z1 L28 Q22 7130 Z1 L28 Q23 7131 Z1 L28 Q24 7132 Z1 L28 Q25 7133 Z1 L28 Q26 7134 Z1 L28 Q27 7135 Z1 L28 Q28 7136 Z1 L28 Q29 7137 Z1 L28 Q30 7138 Z1 L28 Q31 7139 Z1 L28 Q32 7140 Z1 L28 Q33 7141 Z1 L28 Q34 7142 Z1 L28 Q35 7143 Z1 L28 Q36 7144 Z1 L28 Q37 7145 Z1 L28 Q38 7146 Z1 L28 Q39 7147 Z1 L28 Q40 7148 Z1 L28 Q41 7149 Z1 L28 Q42 7150 Z1 L28 Q43 7151 Z1 L28 Q44 7152 Z1 L28 Q45 7153 Z1 L28 Q46 7154 Z1 L28 Q47 7155 Z1 L28 Q48 7156 Z1 L28 Q49 7157 Z1 L28 Q50 7158 Z1 L28 Q51 7159 Z1 L28 Q52 7160 Z1 L28 Q53 7161 Z1 L28 Q54 7162 Z1 L28 Q55 7163 Z1 L28 Q56 7164 Z1 L28 Q57 7165 Z1 L28 Q58 7166 Z1 L28 Q59 7167 Z1 L28 Q60 7168 Z1 L28 Q61 7169 Z1 L28 Q62 7170 Z1 L28 Q63 7171 Z1 L28 Q64 7172 Z1 L28 Q65 7173 Z1 L28 Q66 7174 Z1 L28 Q67 7175 Z1 L28 Q68 7176 Z1 L28 Q69 7177 Z1 L28 Q70 7178 Z1 L28 Q71 7179 Z1 L28 Q72 7180 Z1 L28 Q73 7181 Z1 L28 Q74 7182 Z1 L28 Q75 7183 Z1 L28 Q76 7184 Z1 L28 Q77 7185 Z1 L28 Q78 7186 Z1 L28 Q79 7187 Z1 L28 Q80 7188 Z1 L28 Q81 7189 Z1 L28 Q82 7190 Z1 L28 Q83 7191 Z1 L28 Q84 7192 Z1 L28 Q85 7193 Z1 L28 Q86 7194 Z1 L28 Q87 7195 Z1 L28 Q88 7196 Z1 L28 Q89 7197 Z1 L28 Q90 7198 Z1 L28 Q91 7199 Z1 L28 Q92 7200 Z1 L28 Q93 7201 Z1 L28 Q94 7202 Z1 L28 Q95 7203 Z1 L28 Q96 7204 Z1 L28 Q97 7205 Z1 L28 Q98 7206 Z1 L28 Q99 7207 Z1 L28 Q100 7208 Z1 L28 Q101

TABLE 1-42 7209 Z1 L28 Q102 7210 Z1 L28 Q103 7211 Z1 L29 Q1 7212 Z1 L29 Q2 7213 Z1 L29 Q3 7214 Z1 L29 Q4 7215 Z1 L29 Q5 7216 Z1 L29 Q6 7217 Z1 L29 Q7 7218 Z1 L29 Q8 7219 Z1 L29 Q9 7220 Z1 L29 Q10 7221 Z1 L29 Q11 7222 Z1 L29 Q12 7223 Z1 L29 Q13 7224 Z1 L29 Q14 7225 Z1 L29 Q15 7226 Z1 L29 Q16 7227 Z1 L29 Q17 7228 Z1 L29 Q18 7229 Z1 L29 Q19 7230 Z1 L29 Q20 7231 Z1 L29 Q21 7232 Z1 L29 Q22 7233 Z1 L29 Q23 7234 Z1 L29 Q24 7235 Z1 L29 Q25 7236 Z1 L29 Q26 7237 Z1 L29 Q27 7238 Z1 L29 Q28 7239 Z1 L29 Q29 7240 Z1 L29 Q30 7241 Z1 L29 Q31 7242 Z1 L29 Q32 7243 Z1 L29 Q33 7244 Z1 L29 Q34 7245 Z1 L29 Q35 7245 Z1 L29 Q36 7247 Z1 L29 Q37 7248 Z1 L29 Q38 7249 Z1 L29 Q39 7250 Z1 L29 Q40 7251 Z1 L29 Q41 7252 Z1 L29 Q42 7253 Z1 L29 Q43 7254 Z1 L29 Q44 7255 Z1 L29 Q45 7256 Z1 L29 Q46 7257 Z1 L29 Q47 7258 Z1 L29 Q48 7259 Z1 L29 Q49 7260 Z1 L29 Q50 7261 Z1 L29 Q51 7262 Z1 L29 Q52 7263 Z1 L29 Q53 7264 Z1 L29 Q54 7265 Z1 L29 Q55 7266 Z1 L29 Q56 7267 Z1 L29 Q57 7268 Z1 L29 Q58 7269 Z1 L29 Q59 7270 Z1 L29 Q60 7271 Z1 L29 Q61 7272 Z1 L29 Q62 7273 Z1 L29 Q63 7274 Z1 L29 Q64 7275 Z1 L29 Q65 7276 Z1 L29 Q66 7277 Z1 L29 Q67 7278 Z1 L29 Q68 7279 Z1 L29 Q69 7280 Z1 L29 Q70 7281 Z1 L29 Q71 7282 Z1 L29 Q72 7283 Z1 L29 Q73 7284 Z1 L29 Q74 7285 Z1 L29 Q75 7286 Z1 L29 Q76 7287 Z1 L29 Q77 7288 Z1 L29 Q78 7289 Z1 L29 Q79 7290 Z1 L29 Q80 7291 Z1 L29 Q81 7292 Z1 L29 Q82 7293 Z1 L29 Q83 7294 Z1 L29 Q84 7295 Z1 L29 Q85 7296 Z1 L29 Q86 7297 Z1 L29 Q87 7298 Z1 L29 Q88 7299 Z1 L29 Q89 7300 Z1 L29 Q90 7301 Z1 L29 Q91 7302 Z1 L29 Q92 7303 Z1 L29 Q93 7304 Z1 L29 Q94 7305 Z1 L29 Q95 7306 Z1 L29 Q96 7307 Z1 L29 Q97 7308 Z1 L29 Q98 7309 Z1 L29 Q99 7310 Z1 L29 Q100 7311 Z1 L29 Q101 7312 Z1 L29 Q102 7313 Z1 L29 Q103 7314 Z1 L30 Q1 7315 Z1 L30 Q2 7316 Z1 L30 Q3 7317 Z1 L30 Q4 7318 Z1 L30 Q5 7319 Z1 L30 Q6 7320 Z1 L30 Q7 7321 Z1 L30 Q8 7322 Z1 L30 Q9 7323 Z1 L30 Q10 7324 Z1 L30 Q11 7325 Z1 L30 Q12 7326 Z1 L30 Q13 7327 Z1 L30 Q14 7328 Z1 L30 Q15 7329 Z1 L30 Q16 7330 Z1 L30 Q17 7331 Z1 L30 Q18 7332 Z1 L30 Q19 7333 Z1 L30 Q20 7334 Z1 L30 Q21 7335 Z1 L30 Q22 7336 Z1 L30 Q23 7337 Z1 L30 Q24 7338 Z1 L30 Q25 7339 Z1 L30 Q26 7340 Z1 L30 Q27 7341 Z1 L30 Q28 7372 Z1 L30 Q29 7343 Z1 L30 Q30 7344 Z1 L30 Q31 7345 Z1 L30 Q32 7346 Z1 L30 Q33 7347 Z1 L30 Q34 7346 Z1 L30 Q35 7349 Z1 L30 Q36 7350 Z1 L30 Q37 7351 Z1 L30 Q38 7352 Z1 L30 Q39 7353 Z1 L30 Q40 7354 Z1 L30 Q41 7355 Z1 L30 Q42 7356 Z1 L30 Q43 7357 Z1 L30 Q44 7358 Z1 L30 Q45 7359 Z1 L30 Q46 7360 Z1 L30 Q47 7361 Z1 L30 Q48 7362 Z1 L30 Q49 7363 Z1 L30 Q50 7364 Z1 L30 Q51 7365 Z1 L30 Q52 7366 Z1 L30 Q53 7367 Z1 L30 Q54 7368 Z1 L30 Q55 7369 Z1 L30 Q56 7370 Z1 L30 Q57 7371 Z1 L30 Q58 7372 Z1 L30 Q59 7373 Z1 L30 Q60 7374 Z1 L30 Q61 7375 Z1 L30 Q62 7376 Z1 L30 Q63 7377 Z1 L30 Q64 7378 Z1 L30 Q65 7379 Z1 L30 Q66 7380 Z1 L30 Q67 7381 Z1 L30 Q68 7382 Z1 L30 Q69 7383 Z1 L30 Q70 7384 Z1 L30 Q71 7385 Z1 L30 Q72 7386 Z1 L30 Q73 7387 Z1 L30 Q74 7388 Z1 L30 Q75 7389 Z1 L30 Q76 7390 Z1 L30 Q77 7391 Z1 L30 Q78 7392 Z1 L30 Q79 7393 Z1 L30 Q80 7394 Z1 L30 Q81 7395 Z1 L30 Q82 7396 Z1 L30 Q83 7397 Z1 L30 Q84 7398 Z1 L30 Q85 7399 Z1 L30 Q86 7400 Z1 L30 Q87 7401 Z1 L30 Q88 7402 Z1 L30 Q89 7403 Z1 L30 Q90 7404 Z1 L30 Q91 7405 Z1 L30 Q92 7406 Z1 L30 Q93 7407 Z1 L30 Q94 7408 Z1 L30 Q95 7409 Z1 L30 Q96

TABLE 1-43 7410 Z1 L30 Q97 7411 Z1 L30 Q98 7412 Z1 L30 Q99 7413 Z1 L30 Q100 7414 Z1 L30 Q101 7415 Z1 L30 Q102 7416 Z1 L30 Q103 7417 Z1 L31 Q1 7418 Z1 L31 Q2 7419 Z1 L34 Q3 7420 Z1 L31 Q4 7421 Z1 L31 Q5 7422 Z1 L31 Q6 7423 Z1 L31 Q7 7424 Z1 L31 Q8 7425 Z1 L31 Q9 7426 Z1 L31 Q10 7427 Z1 L31 Q11 7428 Z1 L31 Q12 7429 Z1 L31 Q13 7430 Z1 L31 Q14 7431 Z1 L31 Q15 7432 Z1 L31 Q16 7433 Z1 L31 Q17 7434 Z1 L31 Q18 7435 Z1 L31 Q19 7436 Z1 L31 Q20 7437 Z1 L31 Q21 /438 Z1 L31 Q22 7439 Z1 L31 Q23 7440 Z1 L31 Q24 7441 Z1 L31 Q25 7442 Z1 L31 Q26 7443 Z1 L31 Q27 7444 Z1 L31 Q28 7445 Z1 L31 Q29 7446 Z1 L31 Q30 7447 Z1 L31 Q31 7448 Z1 L31 Q32 7449 Z1 L3I Q33 7450 Z1 L31 Q34 7451 Z1 L31 Q35 7452 Z1 L31 Q36 7453 Z1 L31 Q37 7454 Z1 L31 Q38 7455 Z1 L31 Q39 7456 Z1 L31 Q40 7457 Z1 L31 Q41 7458 Z1 L31 Q42 7459 Z1 L31 Q43 7460 Z1 L31 Q44 7461 Z1 L31 Q45 7462 Z1 L31 Q46 7463 Z1 L31 Q47 7464 Z1 L31 Q48 7465 Z1 L31 Q49 7466 Z1 L31 Q50 7467 Z1 L31 Q51 7468 Z1 L31 Q52 7469 Z1 L31 Q53 7470 Z1 L31 Q54 7471 Z1 L31 Q55 7472 Z1 L31 Q56 7473 Z1 L31 Q57 7474 Z1 L31 Q58 7475 Z1 L31 Q59 7476 Z1 L31 Q60 7477 Z1 L31 Q61 7478 Z1 L31 Q62 7479 Z1 L31 Q63 7480 Z1 L31 Q64 7481 Z1 L31 Q65 7482 Z1 L31 Q66 7483 Z1 L31 Q67 7484 Z1 L31 Q68 7485 Z1 L31 Q69 7486 Z1 L31 Q70 7487 Z1 L31 Q71 7488 Z1 L31 Q72 7489 Z1 L31 Q73 7490 Z1 L31 Q74 7491 Z1 L31 Q75 7492 Z1 L31 Q76 7493 Z1 L31 Q77 7494 Z1 L31 Q78 7495 Z1 L31 Q79 7496 Z1 L31 Q80 7497 Z1 L31 Q81 7498 Z1 L31 Q82 7499 Z1 L31 Q83 7500 Z1 L31 Q84 7501 Z1 L31 Q85 7502 Z1 L31 Q86 7503 Z1 L31 Q87 7504 Z1 L31 Q88 7505 Z1 L31 Q89 7506 Z1 L31 Q90 7507 Z1 L31 Q91 7508 Z1 L31 Q92 7509 Z1 L31 Q93 7510 Z1 L31 Q94 7511 Z1 L31 Q95 7512 Z1 L31 Q96 7513 Z1 L31 Q97 7514 Z1 L31 Q98 7515 Z1 L31 Q99 7516 Z1 L31 Q100 7517 Z1 L31 Q101 7518 Z1 L31 Q102 7519 Z1 L31 Q103 7520 Z1 L32 Q1 7521 Z1 L32 Q2 7522 Z1 L32 Q3 7523 Z1 L32 Q4 7524 Z1 L32 Q5 7525 Z1 L32 Q6 7526 Z1 L32 Q7 7527 Z1 L32 Q8 7528 Z1 L32 Q9 7529 Z1 L32 Q10 7530 Z1 L32 Q11 7531 Z1 L32 Q12 7532 Z1 L32 Q13 7533 Z1 L32 Q14 7534 Z1 L32 Q15 7535 Z1 L32 Q16 7536 Z1 L32 Q17 7537 Z1 L32 Q18 7538 Z1 L32 Q19 7539 Z1 L32 Q20 7540 Z1 L32 Q21 7541 Z1 L32 Q22 7542 Z1 L32 Q23 7543 Z1 L32 Q24 7544 Z1 L32 Q25 7545 Z1 L32 Q26 7546 Z1 L32 Q27 7547 Z1 L32 Q28 7548 Z1 L32 Q29 7549 Z1 L32 Q30 7550 Z1 L32 Q31 7551 Z1 L32 Q32 7552 Z1 L32 Q33 7553 Z1 L32 Q34 7554 Z1 L32 Q35 7555 Z1 L32 Q36 7556 Z1 L32 Q37 7557 Z1 L32 Q38 7558 Z1 L32 Q39 7559 Z1 L32 Q40 7560 Z1 L32 Q41 7561 Z1 L32 Q42 7562 Z1 L32 Q43 7563 Z1 L32 Q44 7564 Z1 L32 Q45 7565 Z1 L32 Q46 7556 Z1 L32 Q47 7567 Z1 L32 Q48 7568 Z1 L32 Q49 7569 Z1 L32 Q50 7570 Z1 L32 Q51 7571 Z1 L32 Q52 7572 Z1 L32 Q53 7573 Z1 L32 Q54 7574 Z1 L32 Q55 7575 Z1 L32 Q56 7576 Z1 L32 Q57 7577 Z1 L32 Q58 7578 Z1 L32 Q59 7579 Z1 L32 Q60 7580 Z1 L32 Q61 7581 Z1 L32 Q62 7582 Z1 L32 Q63 7583 Z1 L32 Q64 7584 Z1 L32 Q65 7585 Z1 L32 Q66 7586 Z1 L32 Q67 7587 Z1 L32 Q68 7588 Z1 L32 Q69 7589 Z1 L32 Q70 7590 Z1 L32 Q71 7591 Z1 L32 Q72 7592 Z1 L32 Q73 7593 Z1 L32 Q74 7594 Z1 L32 Q75 7595 Z1 L32 Q76 7596 Z1 L32 Q77 7597 Z1 L32 Q78 7598 Z1 L32 Q79 7599 Z1 L32 Q80 7600 Z1 L32 Q81 7601 Z1 L32 Q82 7602 Z1 L32 Q83 7603 Z1 L32 Q84 7604 Z1 L32 Q85 7605 Z1 L32 Q86 7606 Z1 L32 Q87 7607 Z1 L32 Q88 7608 Z1 L32 Q89 7609 Z1 L32 Q90 7610 Z1 L32 Q91

TABLE 1-44 7611 Z1 L32 Q92 7612 Z1 L32 Q93 7613 Z1 L32 Q94 7614 Z1 L32 Q95 7615 Z1 L32 Q96 7616 Z1 L32 Q97 7617 Z1 L32 Q98 7618 Z1 L32 Q99 7619 Z1 L32 Q100 7620 Z1 L32 Q101 7621 Z1 L32 Q102 7677 Z1 L37 Q103 7623 Z1 L33 Q1 7624 Z1 L33 Q2 7625 Z1 L33 Q3 7626 Z1 L33 Q4 7627 Z1 L33 Q5 7628 Z1 L33 Q6 7629 Z1 L33 Q7 7630 Z1 L33 Q8 7631 Z1 L33 Q9 7632 Z1 L33 Q10 7633 Z1 L33 Q11 7634 Z1 L33 Q12 7635 Z1 L33 Q13 7636 Z1 L33 Q14 7637 Z1 L33 Q15 7638 Z1 L33 Q16 7639 Z1 L33 Q17 7640 Z1 L33 Q18 7641 Z1 L33 Q19 7642 Z1 L33 Q20 7643 Z1 L33 Q21 7644 Z1 L33 Q22 7645 Z1 L33 Q23 7646 Z1 L33 Q24 7647 Z1 L33 Q25 7648 Z1 L33 Q26 7649 Z1 L33 Q27 7650 Z1 L33 Q28 7651 Z1 L33 Q29 7652 Z1 L33 Q30 7653 Z1 L33 Q31 7654 Z1 L33 Q32 7655 Z1 L33 Q33 7656 Z1 L33 Q34 7657 Z1 L33 Q35 7658 Z1 L33 Q36 7659 Z1 L33 Q37 7660 Z1 L33 Q38 7661 Z1 L33 Q39 7662 Z1 L33 Q40 7663 Z1 L33 Q41 7664 Z1 L33 Q42 7665 Z1 L33 Q43 7666 Z1 L33 Q44 7667 Z1 L33 Q45 7668 Z1 L33 Q46 7669 Z1 L33 Q47 7670 Z1 L33 Q48 7671 Z1 L33 Q49 7672 Z1 L33 Q50 7673 Z1 L33 Q51 7674 Z1 L33 Q52 7675 Z1 L33 Q53 7676 Z1 L33 Q54 7677 Z1 L33 Q55 7678 Z1 L33 Q56 7679 Z1 L33 Q57 7680 Z1 L33 Q58 7681 Z1 L33 Q59 7682 Z1 L33 Q60 7683 Z1 L33 Q61 7684 Z1 L33 Q62 7685 Z1 L33 Q63 7686 Z1 L33 Q64 7687 Z1 L33 Q65 7688 Z1 L33 Q66 7689 Z1 L33 Q67 7690 Z1 L33 Q68 7691 Z1 L33 Q69 7692 Z1 L33 Q70 7693 Z1 L33 Q71 7694 Z1 L33 Q72 7695 Z1 L33 Q73 7696 Z1 L33 Q74 7697 Z1 L33 Q75 7698 Z1 L33 Q76 7699 Z1 L33 Q77 7700 Z1 L33 Q78 7701 Z1 L33 Q79 7702 Z1 L33 Q80 7703 Z1 L33 Q81 7704 Z1 L33 Q82 7705 Z1 L33 Q83 7706 Z1 L33 Q84 7707 Z1 L33 Q85 7708 Z1 L33 Q86 7709 Z1 L33 Q87 7710 Z1 L33 Q88 7711 Z1 L33 Q89 7712 Z1 L33 Q90 7713 Z1 L33 Q91 7714 Z1 L33 Q92 7715 Z1 L33 Q93 7716 Z1 L33 Q94 7717 Z1 L33 Q95 7718 Z1 L33 Q96 7719 Z1 L33 Q97 7720 Z1 L33 Q98 7721 Z1 L33 Q99 7722 Z1 L33 Q100 7723 Z1 L33 Q101 7724 Z1 L33 Q102 7725 Z1 L33 Q103 7726 Z1 L34 Q1 7727 Z1 L34 Q2 7728 Z1 L34 Q3 7729 Z1 L34 Q4 7730 Z1 L34 Q5 7731 Z1 L34 Q6 7732 Z1 L34 Q7 7733 Z1 L34 Q8 7734 Z1 L34 Q9 7735 Z1 L34 Q10 7736 Z1 L34 Q11 7737 Z1 L34 Q12 7738 Z1 L34 Q13 7739 Z1 L34 Q14 7740 Z1 L34 Q15 7741 Z1 L34 Q16 7742 Z1 L34 Q17 7743 Z1 L34 Q18 7744 Z1 L34 Q19 7745 Z1 L34 Q20 7746 Z1 L34 Q21 7747 Z1 L34 Q22 7748 Z1 L34 Q23 7749 Z1 L34 Q24 7750 Z1 L34 Q25 7751 Z1 L34 Q26 7752 Z1 L34 Q27 7753 Z1 L34 Q28 7754 Z1 L34 Q29 7755 Z1 L34 Q30 7756 Z1 L34 Q31 7757 Z1 L34 Q32 7758 Z1 L34 Q33 7759 Z1 L34 Q34 7760 Z1 L34 Q35 7761 Z1 L34 Q36 7762 Z1 L34 Q37 7763 Z1 L34 Q38 7764 Z1 L34 Q39 7765 Z1 L34 Q40 7766 Z1 L34 Q41 7767 Z1 L34 Q42 7768 Z1 L34 Q43 7769 Z1 L34 Q44 7770 Z1 L34 Q45 7771 Z1 L34 Q46 7772 Z1 L34 Q47 7773 Z1 L34 Q48 7774 Z1 L34 Q49 7775 Z1 L34 Q50 7776 Z1 L34 Q51 7777 Z1 L34 Q52 7778 Z1 L34 Q53 7779 Z1 L34 Q54 7780 Z1 L34 Q55 7781 Z1 L34 Q56 7782 Z1 L34 Q57 7783 Z1 L34 Q58 7784 Z1 L34 Q59 7785 Z1 L34 Q60 7786 Z1 L34 Q61 7787 Z1 L34 Q62 7788 Z1 L34 Q63 7789 Z1 L34 Q64 7790 Z1 L34 Q65 7791 Z1 L34 Q66 7792 Z1 L34 Q67 7793 Z1 L34 Q68 7794 Z1 L34 Q69 7795 Z1 L34 Q70 7796 Z1 L34 Q71 7797 Z1 L34 Q72 7798 Z1 L34 Q73 7799 Z1 L34 Q74 7800 Z1 L34 Q75 7801 Z1 L34 Q76 7802 Z1 L34 Q77 7803 Z1 L34 Q78 7804 Z1 L34 Q79 7805 Z1 L34 Q80 7806 Z1 L34 Q81 7807 Z1 L34 Q82 7808 Z1 L34 Q83 7809 Z1 L34 Q84 7810 Z1 L34 Q85 7811 Z1 L34 Q86

TABLE 1-45 7812 Z1 L34 Q87 7813 Z1 L34 Q88 7814 Z1 L34 Q89 7815 Z1 L34 Q90 7816 Z1 L34 Q91 7817 Z1 L34 Q92 7818 Z1 L34 Q93 7819 Z1 L34 Q94 7820 Z1 L34 Q95 7821 Z1 L34 Q96 7822 Z1 L34 Q97 7823 Z1 L34 Q98 7824 Z1 L34 Q99 7825 Z1 L34 Q100 7826 Z1 L34 Q101 7827 Z1 L34 Q102 7828 Z1 L34 Q103 7829 Z1 L35 Q1 7830 Z1 L35 Q2 7831 Z1 L35 Q3 7832 Z1 L35 Q4 7833 Z1 L35 Q5 7834 Z1 L35 Q6 7835 Z1 L35 Q7 7836 Z1 L35 Q8 7837 Z1 L35 Q9 7838 Z1 L35 Q10 7839 Z1 L35 Q11 7840 Z1 L35 Q12 7841 Z1 L35 Q13 7842 Z1 L35 Q14 7843 Z1 L35 Q15 7844 Z1 L35 Q16 7845 Z1 L35 Q17 7846 Z1 L35 Q18 7847 Z1 L35 Q19 7848 Z1 L35 Q20 7849 Z1 L35 Q21 7850 Z1 L35 Q22 7851 Z1 L35 Q23 7852 Z1 L35 Q24 7853 Z1 L35 Q25 7854 Z1 L35 Q26 7855 Z1 L35 Q27 7856 Z1 L35 Q28 7857 Z1 L35 Q29 7858 Z1 L35 Q30 7859 Z1 L35 Q31 7860 Z1 L35 Q32 7861 Z1 L35 Q33 7862 Z1 L35 Q34 7863 Z1 L35 Q35 7864 Z1 L35 Q36 7865 Z1 L35 Q37 7866 Z1 L35 Q38 7867 Z1 L35 Q39 7868 Z1 L35 Q40 7869 Z1 L35 Q41 7870 Z1 L35 Q42 7871 Z1 L35 Q43 7872 Z1 L35 Q44 7873 Z1 L35 Q45 7874 Z1 L35 Q46 7875 Z1 L35 Q47 7876 Z1 L35 Q48 7877 Z1 L35 Q49 7878 Z1 L35 Q50 7879 Z1 L35 Q51 7880 Z1 L35 Q52 7881 Z1 L35 Q53 7882 Z1 L35 Q54 7883 Z1 L35 Q55 7884 Z1 L35 Q56 7885 Z1 L35 Q57 7886 Z1 L35 Q58 7887 Z1 L35 Q59 7888 Z1 L35 Q60 7889 Z1 L35 Q61 7890 Z1 L35 Q62 7891 Z1 L35 Q63 7892 Z1 L35 Q64 7893 Z1 L35 Q65 7894 Z1 L35 Q66 7895 Z1 L35 Q67 7896 Z1 L35 Q68 7897 Z1 L35 Q69 7898 Z1 L35 Q70 7899 Z1 L35 Q71 7900 Z1 L35 Q72 7901 Z1 L35 Q73 7902 Z1 L35 Q74 7903 Z1 L35 Q75 7904 Z1 L35 Q76 7905 Z1 L35 Q77 7906 Z1 L35 Q78 7907 Z1 L35 Q79 7908 Z1 L35 Q80 7909 Z1 L35 Q81 7910 Z1 L35 Q82 7911 Z1 L35 Q83 7912 Z1 L35 Q84 7913 Z1 L35 Q85 7914 Z1 L35 Q86 7915 Z1 L35 Q87 7916 Z1 L35 Q88 7917 Z1 L35 Q89 7918 Z1 L35 Q90 7919 Z1 L35 Q91 7920 Z1 L35 Q92 7921 Z1 L35 Q93 7922 Z1 L35 Q94 7923 Z1 L35 Q95 7924 Z1 L35 Q96 7925 Z1 L35 Q97 7926 Z1 L35 Q98 7927 Z1 L35 Q99 7928 Z1 L35 Q100 7929 Z1 L35 Q101 7930 Z1 L35 Q102 7931 Z1 L35 Q103 7932 Z1 L36 Q1 7933 Z1 L36 Q2 7934 Z1 L36 Q3 7935 Z1 L36 Q4 7936 Z1 L36 Q5 7937 Z1 L36 Q6 7938 Z1 L36 Q7 7939 Z1 L36 Q8 7940 Z1 L36 Q9 7941 Z1 L36 Q10 7942 Z1 L36 Q11 7943 Z1 L36 Q12 7944 Z1 L36 Q13 7945 Z1 L36 Q14 7946 Z1 L36 Q15 7947 Z1 L36 Q16 7948 Z1 L36 Q17 7949 Z1 L36 Q18 7950 Z1 L36 Q19 7951 Z1 L36 Q20 7952 Z1 L36 Q21 7953 Z1 L36 Q22 7954 Z1 L36 Q23 7955 Z1 L36 Q24 7956 Z1 L36 Q25 7957 Z1 L36 Q26 7958 Z1 L36 Q27 7959 Z1 L36 Q28 7960 Z1 L36 Q29 7961 Z1 L36 Q30 7962 Z1 L36 Q31 7963 Z1 L36 Q32 7964 Z1 L36 Q33 7965 Z1 L36 Q34 7966 Z1 L36 Q35 7967 Z1 L36 Q36 7968 Z1 L36 Q37 7969 Z1 L36 Q38 7970 Z1 L36 Q39 7971 Z1 L36 Q40 7972 Z1 L36 Q41 7973 Z1 L36 Q42 7974 Z1 L36 Q43 7975 Z1 L36 Q44 7976 Z1 L36 Q45 7977 Z1 L36 Q46 7978 Z1 L36 Q47 7979 Z1 L36 Q48 7980 Z1 L36 Q49 7981 Z1 L36 Q50 7982 Z1 L36 Q51 7983 Z1 L36 Q52 7984 Z1 L36 Q53 7985 Z1 L36 Q54 7986 Z1 L36 Q55 7987 Z1 L36 Q56 7988 Z1 L36 Q57 7989 Z1 L36 Q58 7990 Z1 L36 Q59 7991 Z1 L36 Q60 7992 Z1 L36 Q61 7993 Z1 L36 Q62 7994 Z1 L36 Q63 7995 Z1 L36 Q64 7996 Z1 L36 Q65 7997 Z1 L36 Q66 7998 Z1 L36 Q67 7999 Z1 L36 Q68 8000 Z1 L36 Q69 8001 Z1 L36 Q70 8002 Z1 L36 Q71 8003 Z1 L36 Q72 8004 Z1 L36 Q73 8005 Z1 L36 Q74 8006 Z1 L36 Q75 8007 Z1 L36 Q76 8008 Z1 L36 Q77 8009 Z1 L36 Q78 8010 Z1 L36 Q79 8011 Z1 L36 Q80 8012 Z1 L36 Q81

TABLE 1-76 8013 Z1 L36 Q82 8014 Z1 L36 Q83 8015 Z1 L36 Q84 8016 Z1 L36 Q85 8017 Z1 L36 Q86 8018 Z1 L36 Q87 8019 Z1 L36 Q88 8020 Z1 L36 Q89 8021 Z1 L36 Q90 8022 Z1 L36 Q91 8023 Z1 L36 Q92 8024 Z1 L36 Q93 8025 Z1 L36 Q94 8026 Z1 L36 Q95 8027 Z1 L36 Q96 8028 Z1 L36 Q97 8029 Z1 L36 Q98 8030 Z1 L36 Q99 8031 Z1 L36 Q100 8032 Z1 L36 Q101 8033 Z1 L36 Q102 8034 Z1 L36 Q103 8035 Z2 L15 Q1 8036 Z2 L15 Q2 8037 Z2 L15 Q3 8038 Z2 L15 Q4 8039 Z2 L15 Q5 8040 Z2 L15 Q6 8041 Z2 L15 Q7 8042 Z2 L15 Q8 8043 Z2 L15 Q9 8044 Z2 L15 Q10 8045 Z2 L15 Q11 8046 Z2 L15 Q12 8047 Z2 L15 Q13 8048 Z2 L15 Q14 8049 Z2 L15 Q15 8050 Z2 L15 Q16 8051 Z2 L15 Q17 8052 Z2 L15 Q18 8053 Z2 L15 Q19 8054 Z2 L15 Q20 8055 Z2 L15 Q21 8056 Z2 L15 Q22 8057 Z2 L15 Q23 8058 Z2 L15 Q24 8059 Z2 L15 Q25 8060 Z2 L15 Q26 8061 Z2 L15 Q27 8062 Z2 L15 Q28 8063 Z2 L15 Q29 8064 Z2 L15 Q30 8065 Z2 L15 Q31 8066 Z2 L15 Q32 8067 Z2 L15 Q33 8068 Z2 L15 Q34 8069 Z2 L15 Q35 8070 Z2 L15 Q36 8071 Z2 L15 Q37 8072 Z2 L15 Q38 8073 Z2 L15 Q39 8074 Z2 L15 Q40 8075 Z2 L15 Q41 8076 Z2 L15 Q42 8077 Z2 L15 Q43 8078 Z2 L15 Q44 8079 Z2 L15 Q45 8080 Z2 L15 Q46 8081 Z2 L15 Q47 8082 Z2 L15 Q48 8083 Z2 L15 Q49 8084 Z2 L15 Q50 8085 Z2 L15 Q51 8086 Z2 L15 Q52 8087 Z2 L15 Q53 8088 Z2 L15 Q54 8089 Z2 L15 Q55 8090 Z2 L15 Q56 8091 Z2 L15 Q57 8092 Z2 L15 Q58 8093 Z2 L15 Q59 8094 Z2 L15 Q60 8095 Z2 L15 Q61 8096 Z2 L15 Q62 8097 Z2 L15 Q63 8098 Z2 L15 Q64 8099 Z2 L15 Q65 8100 Z2 L15 Q66 8101 Z2 L15 Q67 8102 Z2 L15 Q68 8103 Z2 L15 Q69 8104 Z2 L15 Q70 8105 Z2 L15 Q71 8106 Z2 L15 Q72 8107 Z2 L15 Q73 8108 Z2 L15 Q74 8109 Z2 L15 Q75 8110 Z2 L15 Q76 8111 Z2 L15 Q77 8112 Z2 L15 Q78 8113 Z2 L15 Q79 8114 Z2 L15 Q80 8115 Z2 L15 Q81 8116 Z2 L15 Q82 8117 Z2 L15 Q83 8118 Z2 L15 Q84 8119 Z2 L15 Q85 8120 Z2 L15 Q86 8121 Z2 L15 Q87 8122 Z2 L15 Q88 8123 Z2 L15 Q89 8124 Z2 L15 Q90 8125 Z2 L15 Q91 8126 Z2 L15 Q92 8127 Z2 L15 Q93 8128 Z2 L15 Q94 8129 Z2 L15 Q95 8130 Z2 L15 Q96 8131 Z2 L15 Q97 8132 Z2 L15 Q98 8133 Z2 L15 Q99 8134 Z2 L15 Q100 8135 Z2 L15 Q101 8136 Z2 L15 Q102 8137 Z2 L15 Q103 8138 Z2 L16 Q1 8139 Z2 L16 Q2 8140 Z2 L16 Q3 8141 Z2 L16 Q4 8142 Z2 L16 Q5 8143 Z2 L16 Q6 8144 Z2 L16 Q7 8145 Z2 L16 Q8 8146 Z2 L16 Q9 8147 Z2 L16 Q10 8148 Z2 L16 Q11 8149 Z2 L16 Q12 8150 Z2 L16 Q13 8151 Z2 L16 Q14 8152 Z2 L16 Q15 8153 Z2 L16 Q16 8154 Z2 L16 Q17 8155 Z2 L16 Q18 8156 Z2 L16 Q19 8157 Z2 L16 Q20 8158 Z2 L16 Q21 8159 Z2 L16 Q22 8160 Z2 L16 Q23 8161 Z2 L16 Q24 8162 Z2 L16 Q25 8163 Z2 L16 Q26 8164 Z2 L16 Q27 8165 Z2 L16 Q28 8166 Z2 L16 Q29 8167 Z2 L16 Q30 8168 Z2 L16 Q31 8169 Z2 L16 Q32 8170 Z2 L16 Q33 8171 Z2 L16 Q34 8172 Z2 L16 Q35 8173 Z2 L16 Q36 8174 Z2 L16 Q37 8175 Z2 L16 Q38 8176 Z2 L16 Q39 8177 Z2 L16 Q40 8178 Z2 L16 Q41 8179 Z2 L16 Q42 8180 Z2 L16 Q43 8181 Z2 L16 Q44 8182 Z2 L16 Q45 8183 Z2 L16 Q46 8184 Z2 L16 Q47 8185 Z2 L16 Q48 8186 Z2 L16 Q49 8187 Z2 L16 Q50 8188 Z2 L16 Q51 8189 Z2 L16 Q52 8190 Z2 L16 Q53 8191 Z2 L16 Q54 8192 Z2 L16 Q55 8193 Z2 L16 Q56 8194 Z2 L16 Q57 8195 Z2 L16 Q58 8186 Z2 L16 Q59 8197 Z2 L16 Q60 8198 Z2 L16 Q61 8199 Z2 L16 Q62 8200 Z2 L16 Q63 8201 Z2 L16 Q64 8202 Z2 L16 Q65 8203 Z2 L16 Q66 8204 Z2 L16 Q67 8205 Z2 L16 Q68 8206 Z2 L16 Q69 8207 Z2 L16 Q70 8208 Z2 L16 Q71 8209 Z2 L16 Q72 8210 Z2 L16 Q73 8211 Z2 L16 Q74 8212 Z2 L16 Q75 8213 Z2 L16 Q76

TABLE 1-47 8214 Z2 L16 Q77 8215 Z2 L16 Q78 8216 Z2 L16 Q79 8217 Z2 L16 Q80 8218 Z2 L16 Q81 8219 Z2 L16 Q82 8220 Z2 L16 Q83 8221 Z2 L16 Q84 8222 Z2 L16 Q85 8223 Z2 L16 Q86 8224 Z2 L16 Q87 8225 Z2 L16 Q88 8226 Z2 L16 Q89 8227 Z2 L16 Q90 8228 Z2 L16 Q91 8229 Z2 L16 Q92 8230 Z2 L16 Q93 8231 Z2 L16 Q94 8232 Z2 L16 Q95 8233 Z2 L16 Q96 8234 Z2 L16 Q97 8235 Z2 L16 Q98 8236 Z2 L16 Q99 8237 Z2 L16 Q100 8238 Z2 L16 Q101 8239 Z2 L16 Q102 8240 Z2 L16 Q103 8241 Z2 L17 Q1 8242 Z2 L17 Q2 8243 Z2 L17 Q3 8244 Z2 L17 Q4 8245 Z2 L17 Q5 8246 Z2 L17 Q6 8247 Z2 L17 Q7 8248 Z2 L17 Q8 8249 Z2 L17 Q9 8250 Z2 L17 Q10 8251 Z2 L17 Q11 8252 Z2 L17 Q12 8253 Z2 L17 Q13 8254 Z2 L17 Q14 8255 Z2 L17 Q15 8256 Z2 L17 Q16 8257 Z2 L17 Q17 8258 Z2 L17 Q18 8259 Z2 L17 Q19 8260 Z2 L17 Q20 8261 Z2 L17 Q21 8262 Z2 L17 Q22 8263 Z2 L17 Q23 8264 Z2 L17 Q24 8265 Z2 L17 Q25 8266 Z2 L17 Q26 8267 Z2 L17 Q27 8268 Z2 L17 Q28 8269 Z2 L17 Q29 8270 Z2 L17 Q30 8271 Z2 L17 Q31 8272 Z2 L17 Q32 8273 Z2 L17 Q33 8274 Z2 L17 Q34 8275 Z2 L17 Q35 8276 Z2 L17 Q36 8277 Z2 L17 Q37 8278 Z2 L17 Q38 8279 Z2 L17 Q39 8280 Z2 L17 Q40 8281 Z2 L17 Q41 8282 Z2 L17 Q42 8283 Z2 L17 Q43 8284 Z2 L17 Q44 8285 Z2 L17 Q45 8286 Z2 L17 Q46 8287 Z2 L17 Q47 8288 Z2 L17 Q48 8289 Z2 L17 Q49 8290 Z2 L17 Q50 8291 Z2 L17 Q51 8292 Z2 L17 Q52 8293 Z2 L17 Q53 8204 Z2 L17 Q54 8295 Z2 L17 Q55 8296 Z2 L17 Q56 8297 Z2 L17 Q57 8298 Z2 L17 Q58 8299 Z2 L17 Q59 8300 Z2 L17 Q60 8301 Z2 L17 Q61 8302 Z2 L17 Q62 8303 Z2 L17 Q63 8304 Z2 L17 Q64 8305 Z2 L17 Q65 8306 Z2 L17 Q66 8307 Z2 L17 Q67 8308 Z2 L17 Q68 8309 Z2 L17 Q69 8310 Z2 L17 Q70 8311 Z2 L17 Q71 8312 Z2 L17 Q72 8313 Z2 L17 Q73 8314 Z2 L17 Q74 8315 Z2 L17 Q75 8316 Z2 L17 Q76 8317 Z2 L17 Q77 8318 Z2 L17 Q78 8319 Z2 L17 Q79 8320 Z2 L17 Q80 8321 Z2 L17 Q81 8322 Z2 L17 Q82 8323 Z2 L17 Q83 8324 Z2 L17 Q84 8325 Z2 L17 Q85 8326 Z2 L17 Q86 8327 Z2 L17 Q87 8328 Z2 L17 Q88 8329 Z2 L17 Q89 8300 Z2 L17 Q90 8331 Z2 L17 Q91 8332 Z2 L17 Q92 8333 Z2 L17 Q93 8334 Z2 L17 Q94 8335 Z2 L17 Q95 8336 Z2 L17 Q96 8337 Z2 L17 Q97 8338 Z2 L17 Q98 8339 Z2 L17 Q99 8340 Z2 L17 Q100 8341 Z2 L17 Q101 8342 Z2 L17 Q102 8343 Z2 L17 Q103 8344 Z2 L18 Q1 8345 Z2 L18 Q2 8346 Z2 L18 Q3 8347 Z2 L18 Q4 8348 Z2 L18 Q5 8349 Z2 L18 Q6 8350 Z2 L18 Q7 8351 Z2 L18 Q8 8352 Z2 L18 Q9 8353 Z2 L18 Q10 8354 Z2 L18 Q11 8355 Z2 L18 Q12 8356 Z2 L18 Q13 8357 Z2 L18 Q14 8358 Z2 L18 Q15 8359 Z2 L18 Q16 8360 Z2 L18 Q17 8361 Z2 L18 Q18 8362 Z2 L18 Q19 8363 Z2 L18 Q20 8364 Z2 L18 Q21 8365 Z2 L18 Q22 8366 Z2 L18 Q23 8367 Z2 L18 Q24 8368 Z2 L18 Q25 8369 Z2 L18 Q26 8370 Z2 L18 Q27 8371 Z2 L18 Q28 8372 Z2 L18 Q29 8373 Z2 L18 Q30 8374 Z2 L18 Q31 8375 Z2 L18 Q32 8376 Z2 L18 Q33 8377 Z2 L18 Q34 8378 Z2 L18 Q35 8379 Z2 L18 Q36 8380 Z2 L18 Q37 8381 Z2 L18 Q38 8382 Z2 L18 Q39 8383 Z2 L18 Q40 8384 Z2 L18 Q41 8385 Z2 L18 Q42 8386 Z2 L18 Q43 8387 Z2 L18 Q44 8388 Z2 L18 Q45 8389 Z2 L18 Q46 8390 Z2 L18 Q47 8391 Z2 L18 Q48 8392 Z2 L18 Q49 8393 Z2 L18 Q50 8394 Z2 L18 Q51 8395 Z2 L18 Q52 8396 Z2 L18 Q53 8397 Z2 L18 Q54 8398 Z2 L18 Q55 8399 Z2 L18 Q56 8400 Z2 L18 Q57 8401 Z2 L18 Q58 8402 Z2 L18 Q59 8403 Z2 L18 Q60 8404 Z2 L18 Q61 8405 Z2 L18 Q62 8406 Z2 L18 Q63 8407 Z2 L18 Q64 8408 Z2 L18 Q65 8409 Z2 L18 Q66 8410 Z2 L18 Q67 8411 Z2 L18 Q68 8412 Z2 L18 Q69 8413 Z2 L18 Q70 8414 Z2 L18 Q71

TABLE 1-48 8415 Z2 L18 Q72 8415 Z2 L18 Q73 8417 Z2 L18 Q74 8418 Z2 L18 Q75 8419 Z2 L18 Q76 8420 Z2 L18 Q77 8421 Z2 L18 Q78 8422 Z2 L18 Q79 8423 Z2 L18 Q80 8424 Z2 L18 Q81 8425 Z2 L18 Q82 8426 Z2 L18 Q83 8427 Z2 L18 Q84 8428 Z2 L18 Q85 8429 Z2 L18 Q86 8430 Z2 L18 Q87 8431 Z2 L18 Q88 8432 Z2 L18 Q89 8433 Z2 L18 Q90 8434 Z2 L18 Q91 8435 Z2 L18 Q92 8435 Z2 L18 Q93 8437 Z2 L18 Q94 8438 Z2 L18 Q95 8439 Z2 L18 Q96 8440 Z2 L18 Q97 8441 Z2 L18 Q98 8442 Z2 L18 Q99 8443 Z2 L18 Q100 3444 Z2 L18 Q101 8445 Z2 L18 Q102 8445 Z2 L18 Q103 8447 Z2 L19 Q1 8448 Z2 L19 Q2 8449 Z2 L19 Q3 8450 Z2 L19 Q4 8451 Z2 L19 Q5 3452 Z2 L19 Q6 8453 Z2 L19 Q7 8454 Z2 L19 Q8 8455 Z2 L19 Q9 8456 Z2 L19 Q10 8457 Z2 L19 Q11 8458 Z2 L19 Q12 8459 Z2 L19 Q13 8460 Z2 L19 Q14 8461 Z2 L19 Q15 8462 Z2 L19 Q16 8463 Z2 L19 Q17 8464 Z2 L19 Q18 8465 Z2 L19 Q19 8466 Z2 L19 Q20 8467 Z2 L19 Q21 8468 Z2 L19 Q22 8469 Z2 L19 Q23 8470 Z2 L19 Q24 8471 Z2 L19 Q25 8472 Z2 L19 Q26 8473 Z2 L19 Q27 8474 Z2 L19 Q28 8475 Z2 L19 Q29 8476 Z2 L19 Q30 8477 Z2 L19 Q31 8478 Z2 L19 Q32 8479 Z2 L19 Q33 8480 Z2 L19 Q34 8481 Z2 L19 Q35 8482 Z2 L19 Q36 8483 Z2 L19 Q37 8484 Z2 L19 Q38 8485 Z2 L19 Q39 8486 Z2 L19 Q40 8487 Z2 L19 Q41 8488 Z2 L19 Q42 8489 Z2 L19 Q43 8490 Z2 L19 Q44 8491 Z2 L19 Q45 8492 Z2 L19 Q46 8493 Z2 L19 Q47 8494 Z2 L19 Q48 8495 Z2 L19 Q49 8496 Z2 L19 Q50 8497 Z2 L19 Q51 8498 Z2 L19 Q52 8499 Z2 L19 Q53 8500 Z2 L19 Q54 8501 Z2 L19 Q55 8502 Z2 L19 Q56 8503 Z2 L19 Q57 8504 Z2 L19 Q58 8505 Z2 L19 Q59 8506 Z2 L19 Q60 8507 Z2 L19 Q61 8508 Z2 L19 Q62 8509 Z2 L19 Q63 8510 Z2 L19 Q64 8511 Z2 L19 Q65 8512 Z2 L19 Q66 8513 Z2 L19 Q67 8514 Z2 L19 Q68 8515 Z2 L19 Q69 8516 Z2 L19 Q70 8517 Z2 L19 Q71 8518 Z2 L19 Q72 8519 Z2 L19 Q73 8520 Z2 L19 Q74 8521 Z2 L19 Q75 8522 Z2 L19 Q76 8523 Z2 L19 Q77 8524 Z2 L19 Q78 8525 Z2 L19 Q79 8526 Z2 L19 Q80 8527 Z2 L19 Q81 8528 Z2 L19 Q82 8529 Z2 L19 Q83 8530 Z2 L19 Q84 8531 Z2 L19 Q85 8532 Z2 L19 Q86 8533 Z2 L19 Q87 8534 Z2 L19 Q88 8535 Z2 L19 Q89 8536 Z2 L19 Q90 8537 Z2 L19 Q91 8538 Z2 L19 Q92 8539 Z2 L19 Q93 8540 Z2 L19 Q94 8541 Z2 L19 Q95 8542 Z2 L19 Q96 8543 Z2 L19 Q97 8544 Z2 L19 Q98 8545 Z2 L19 Q99 8546 Z2 L19 Q100 8547 Z2 L19 Q101 8548 Z2 L19 Q102 8549 Z2 L19 Q103 8550 Z2 L20 Q1 8551 Z2 L20 Q2 8552 Z2 L20 Q3 8553 Z2 L20 Q4 8554 Z2 L20 Q5 8555 Z2 L20 Q6 8556 Z2 L20 Q7 8557 Z2 L20 Q8 8558 Z2 L20 Q9 8559 Z2 L20 Q10 8560 Z2 L20 Q11 8561 Z2 L20 Q12 8562 Z2 L20 Q13 8563 Z2 L20 Q14 8564 Z2 L20 Q15 8565 Z2 L20 Q16 8566 Z2 L20 Q17 8567 Z2 L20 Q18 8568 Z2 L20 Q19 8569 Z2 L20 Q20 8570 Z2 L20 Q21 8571 Z2 L20 Q22 8572 Z2 L20 Q23 8573 Z2 L20 Q24 8574 Z2 L20 Q25 8575 Z2 L20 Q26 8576 Z2 L20 Q27 8577 Z2 L20 Q28 8578 Z2 L20 Q29 8579 Z2 L20 Q30 8580 Z2 L20 Q31 8581 Z2 L20 Q32 8582 Z2 L20 Q33 8583 Z2 L20 Q34 8584 Z2 L20 Q35 8585 Z2 L20 Q36 8586 Z2 L20 Q37 8587 Z2 L20 Q38 8588 Z2 L20 Q39 8589 Z2 L20 Q40 8590 Z2 L20 Q41 8591 Z2 L20 Q42 8592 Z2 L20 Q43 8593 Z2 L20 Q44 8594 Z2 L20 Q45 8595 Z2 L20 Q46 8596 Z2 L20 Q47 8597 Z2 L20 Q48 8598 Z2 L20 Q49 8599 Z2 L20 Q50 8600 Z2 L20 Q51 8601 Z2 L20 Q52 8602 Z2 L20 Q53 8603 Z2 L20 Q54 8604 Z2 L20 Q55 8605 Z2 L20 Q56 8606 Z2 L20 Q57 8607 Z2 L20 Q58 8608 Z2 L20 Q59 8609 Z2 L20 Q60 8610 Z2 L20 Q61 8611 Z2 L20 Q62 8612 Z2 L20 Q63 8613 Z2 L20 Q64 8614 Z2 L20 Q65 8615 Z2 L20 Q66

TABLE 1-49 8616 Z2 L20 Q67 8617 Z2 L20 Q68 8618 Z2 L20 Q69 8619 Z2 L20 Q70 8620 Z2 L20 Q71 8621 Z2 L20 Q72 8622 Z2 L20 Q73 8623 Z2 L20 Q74 8624 Z2 L20 Q75 8625 Z2 L20 Q76 8626 Z2 L20 Q77 8627 Z2 L20 Q78 8628 Z2 L20 Q79 8629 Z2 L20 Q80 8630 Z2 L20 Q81 8631 Z2 L20 Q82 8632 Z2 L20 Q83 8633 Z2 L20 Q84 8634 Z2 L20 Q85 8635 Z2 L20 Q86 8636 Z2 L20 Q87 8637 Z2 L20 Q88 8638 Z2 L20 Q89 8639 Z2 L20 Q90 8640 Z2 L20 Q91 8641 Z2 L20 Q92 8642 Z2 L20 Q93 8643 Z2 L20 Q94 8644 Z2 L20 Q95 8645 Z2 L20 Q96 8646 Z2 L20 Q97 8647 Z2 L20 Q98 8648 Z2 L20 Q99 8649 Z2 L20 Q100 8650 Z2 L20 Q101 8651 Z2 L20 Q102 8652 Z2 L20 Q103 8653 Z2 L21 Q1 8654 Z2 L21 Q2 8655 Z2 L21 Q3 8656 Z2 L21 Q4 8657 Z2 L21 Q5 8658 Z2 L21 Q6 8659 Z2 L21 Q7 8660 Z2 L21 Q8 8661 Z2 L21 Q9 8662 Z2 L21 Q10 8663 Z2 L21 Q11 8664 Z2 L21 Q12 8665 Z2 L21 Q13 8666 Z2 L21 Q14 8667 Z2 L21 Q15 8668 Z2 L21 Q16 8669 Z2 L21 Q17 8670 Z2 L21 Q18 8671 Z2 L21 Q19 8672 Z2 L21 Q20 8673 Z2 L21 Q21 8674 Z2 L21 Q22 8675 Z2 L21 Q23 8676 Z2 L21 Q24 8677 Z2 L21 Q25 8678 Z2 L21 Q26 8679 Z2 L21 Q27 8680 Z2 L21 Q28 8671 Z2 L21 Q29 8682 Z2 L21 Q30 8683 Z2 L21 Q31 8684 Z2 L21 Q32 8685 Z2 L21 Q33 8686 Z2 L21 Q34 8687 Z2 L21 Q35 8688 Z2 L21 Q36 8689 Z2 L21 Q37 8690 Z2 L21 Q38 8691 Z2 L21 Q39 8692 Z2 L21 Q40 8693 Z2 L21 Q41 8694 Z2 L21 Q42 8695 Z2 L21 Q43 8696 Z2 L21 Q44 8697 Z2 L21 Q45 8698 Z2 L21 Q46 8699 Z2 L21 Q47 8700 Z2 L21 Q48 8701 Z2 L21 Q49 8702 Z2 L21 Q50 8703 Z2 L21 Q51 8704 Z2 L21 Q52 8705 Z2 L21 Q53 8706 Z2 L21 Q54 8707 Z2 L21 Q55 8708 Z2 L21 Q56 8709 Z2 L21 Q57 8710 Z2 L21 Q58 8711 Z2 L21 Q59 8712 Z2 L21 Q60 8713 Z2 L21 Q61 8714 Z2 L21 Q62 8715 Z2 L21 Q63 8716 Z2 L21 Q64 8717 Z2 L21 Q65 8718 Z2 L21 Q66 8719 Z2 L21 Q67 8720 Z2 L21 Q68 8721 Z2 L21 Q69 8722 Z2 L21 Q70 8723 Z2 L21 Q71 8724 Z2 L21 Q72 8725 Z2 L21 Q73 8726 Z2 L21 Q74 8727 Z2 L21 Q75 8728 Z2 L21 Q76 8729 Z2 L21 Q77 8730 Z2 L21 Q78 8731 Z2 L21 Q79 8732 Z2 L21 Q80 8733 Z2 L21 Q81 8734 Z2 L21 Q82 8735 Z2 L21 Q83 8736 Z2 L21 Q84 8737 Z2 L21 Q85 8738 Z2 L21 Q86 8739 Z2 L21 Q87 8740 Z2 L21 Q88 8741 Z2 L21 Q89 8742 Z2 L21 Q90 8743 Z2 L21 Q91 8744 Z2 L21 Q92 8745 Z2 L21 Q93 8746 Z2 L21 Q94 8747 Z2 L21 Q95 8748 Z2 L21 Q96 8749 Z2 L21 Q97 8750 Z2 L21 Q98 8751 Z2 L21 Q99 8752 Z2 L21 Q100 8753 Z2 L21 Q101 8754 Z2 L21 Q102 8755 Z2 L21 Q103 8756 Z2 L22 Q1 8757 Z2 L22 Q2 8758 Z2 L22 Q3 8759 Z2 L22 Q4 8760 Z2 L22 Q5 8761 Z2 L22 Q6 8762 Z2 L22 Q7 8763 Z2 L22 Q8 8764 Z2 L22 Q9 8765 Z2 L22 Q10 8766 Z2 L22 Q11 8767 Z2 L22 Q12 8768 Z2 L22 Q13 8769 Z2 L22 Q14 8770 Z2 L22 Q15 8771 Z2 L22 Q16 8772 Z2 L22 Q17 8773 Z2 L22 Q18 8774 Z2 L22 Q19 8775 Z2 L22 Q20 8776 Z2 L22 Q21 8777 Z2 L22 Q22 8778 Z2 L22 Q23 8779 Z2 L22 Q24 8780 Z2 L22 Q25 8781 Z2 L22 Q26 8782 Z2 L22 Q27 8783 Z2 L22 Q28 8784 Z2 L22 Q29 8785 Z2 L22 Q30 8786 Z2 L22 Q31 8787 Z2 L22 Q32 8788 Z2 L22 Q33 8789 Z2 L22 Q34 8790 Z2 L22 Q35 8791 Z2 L22 Q36 8792 Z2 L22 Q37 8793 Z2 L22 Q38 8794 Z2 L22 Q39 8795 Z2 L22 Q40 8796 Z2 L22 Q41 8797 Z2 L22 Q42 8798 Z2 L22 Q43 8799 Z2 L22 Q44 8800 Z2 L22 Q45 8801 Z2 L22 Q46 8802 Z2 L22 Q47 8803 Z2 L22 Q48 8804 Z2 L22 Q49 8805 Z2 L22 Q50 8806 Z2 L22 Q51 8807 Z2 L22 Q52 8808 Z2 L22 Q53 8809 Z2 L22 Q54 8810 Z2 L22 Q55 8811 Z2 L22 Q56 8812 Z2 L22 Q57 8813 Z2 L22 Q58 8814 Z2 L22 Q59 8815 Z2 L22 Q60 8816 Z2 L22 Q61

TABLE 1-50 8817 Z2 L22 Q62 8818 Z2 L22 Q63 8819 Z2 L22 Q64 8820 Z2 L22 Q65 8821 Z2 L22 Q66 8822 Z2 L22 Q67 8823 Z2 L22 Q68 8824 Z2 L22 Q69 8825 Z2 L22 Q70 8826 Z2 L22 Q71 8827 Z2 L22 Q72 8828 Z2 L22 Q73 8829 Z2 L22 Q74 8830 Z2 L22 Q75 8831 Z2 L22 Q76 8832 Z2 L22 Q77 8833 Z2 L22 Q78 8834 Z2 L22 Q79 8835 Z2 L22 Q80 8836 Z2 L22 Q81 8837 Z2 L22 Q82 8838 Z2 L22 Q83 8839 Z2 L22 Q84 8840 Z2 L22 Q85 8841 Z2 L22 Q86 8842 Z2 L22 Q87 8843 Z2 L22 Q88 8844 Z2 L22 Q89 8845 Z2 L22 Q90 8846 Z2 L22 Q91 8847 Z2 L22 Q92 8848 Z2 L22 Q93 8849 Z2 L22 Q94 8850 Z2 L22 Q95 8851 Z2 L22 Q96 8852 Z2 L22 Q97 8853 Z2 L22 Q98 8854 Z2 L22 Q99 8855 Z2 L22 Q100 8856 Z2 L22 Q101 8857 Z2 L22 Q102 8858 Z2 L22 Q103 8859 Z2 L23 Q1 8860 Z2 L23 Q2 8861 Z2 L23 Q3 8862 Z2 L23 Q4 8863 Z2 L23 Q5 8864 Z2 L23 Q6 8865 Z2 L23 Q7 8866 Z2 L23 Q8 8867 Z2 L23 Q9 8868 Z2 L23 Q10 8869 Z2 L23 Q11 8870 Z2 L23 Q12 8871 Z2 L23 Q13 8872 Z2 L23 Q14 8873 Z2 L23 Q15 8874 Z2 L23 Q16 8875 Z2 L23 Q17 8876 Z2 L23 Q18 8877 Z2 L23 Q19 8878 Z2 L23 Q20 8879 Z2 L23 Q21 8880 Z2 L23 Q22 8881 Z2 L23 Q23 8882 Z2 L23 Q24 8883 Z2 L23 Q25 8884 Z2 L23 Q26 8885 Z2 L23 Q27 8886 Z2 L23 Q28 8887 Z2 L23 Q29 8888 Z2 L23 Q30 8889 Z2 L23 Q31 8890 Z2 L23 Q32 8891 Z2 L23 Q33 8892 Z2 L23 Q34 8893 Z2 L23 Q35 8894 Z2 L23 Q36 8895 Z2 L23 Q37 8896 Z2 L23 Q38 8897 Z2 L23 Q39 8898 Z2 L23 Q40 8899 Z2 L23 Q41 8900 Z2 L23 Q42 8901 Z2 L23 Q43 8902 Z2 L23 Q44 8903 Z2 L23 Q45 8904 Z2 L23 Q46 8905 Z2 L23 Q47 8906 Z2 L23 Q48 8907 Z2 L23 Q49 8908 Z2 L23 Q50 8909 Z2 L23 Q51 8910 Z2 L23 Q52 8911 Z2 L23 Q53 8912 Z2 L23 Q54 8913 Z2 L23 Q55 8914 Z2 L23 Q56 8915 Z2 L23 Q57 8916 Z2 L23 Q58 8917 Z2 L23 Q59 8918 Z2 L23 Q60 8919 Z2 L23 Q61 8920 Z2 L23 Q62 8921 Z2 L23 Q63 8922 Z2 L23 Q64 8923 Z2 L23 Q65 8924 Z2 L23 Q66 8925 Z2 L23 Q67 8926 Z2 L23 Q68 8927 Z2 L23 Q69 8928 Z2 L23 Q70 8929 Z2 L23 Q71 8930 Z2 L23 Q72 8931 Z2 L23 Q73 8932 Z2 L23 Q74 8933 Z2 L23 Q75 8934 Z2 L23 Q76 8935 Z2 L23 Q77 8936 Z2 L23 Q78 8937 Z2 L23 Q79 8938 Z2 L23 Q80 8939 Z2 L23 Q81 8940 Z2 L23 Q82 8941 Z2 L23 Q83 8942 Z2 L23 Q84 8943 Z2 L23 Q85 8944 Z2 L23 Q86 8945 Z2 L23 Q87 8946 Z2 L23 Q88 8947 Z2 L23 Q89 8948 Z2 L23 Q90 8949 Z2 L23 Q91 8950 Z2 L23 Q92 8951 Z2 L23 Q93 8952 Z2 L23 Q94 8953 Z2 L23 Q95 8954 Z2 L23 Q96 8955 Z2 L23 Q97 8956 Z2 L23 Q98 8957 Z2 L23 Q99 8958 Z2 L23 Q100 8959 Z2 L23 Q101 8960 Z2 L23 Q102 8961 Z2 L23 Q103 8962 Z2 L24 Q1 8963 Z2 L24 Q2 8964 Z2 L24 Q3 8965 Z2 L24 Q4 8966 Z2 L24 Q5 8967 Z2 L24 Q6 8968 Z2 L24 Q7 8969 Z2 L24 Q8 8970 Z2 L24 Q9 8971 Z2 L24 Q10 8972 Z2 L24 Q11 8973 Z2 L24 Q12 8974 Z2 L24 Q13 8975 Z2 L24 Q14 8976 Z2 L24 Q15 8977 Z2 L24 Q16 8978 Z2 L24 Q17 8979 Z2 L24 Q18 8980 Z2 L24 Q19 8981 Z2 L24 Q20 8982 Z2 L24 Q21 8983 Z2 L24 Q22 8984 Z2 L24 Q23 8985 Z2 L24 Q24 8986 Z2 L24 Q25 8987 Z2 L24 Q26 8988 Z2 L24 Q27 8989 Z2 L24 Q28 8990 Z2 L24 Q29 8991 Z2 L24 Q30 8992 Z2 L24 Q31 8993 Z2 L24 Q32 8994 Z2 L24 Q33 8995 Z2 L24 Q34 8996 Z2 L24 Q35 8997 Z2 L24 Q36 8998 Z2 L24 Q37 8999 Z2 L24 Q38 9000 Z2 L24 Q39 9001 Z2 L24 Q40 9002 Z2 L24 Q41 9003 Z2 L24 Q42 9004 Z2 L24 Q43 9005 Z2 L24 Q44 9006 Z2 L24 Q45 9007 Z2 L24 Q46 9008 Z2 L24 Q47 9009 Z2 L24 Q48 9010 Z2 L24 Q49 9011 Z2 L24 Q50 9012 Z2 L24 Q51 9013 Z2 L24 Q52 9014 Z2 L24 Q53 9015 Z2 L24 Q54 9016 Z2 L24 Q55 9017 Z2 L24 Q56

TABLE 1-51 9018 Z2 L24 Q57 9019 Z2 L24 Q58 9020 Z2 L24 Q59 9021 Z2 L24 Q60 9022 Z2 L24 Q61 9023 Z2 L24 Q62 9024 Z2 L24 Q63 9025 Z2 L24 Q64 9026 Z2 L24 Q65 9027 Z2 L24 Q66 9028 Z2 L24 Q67 9029 Z2 L24 Q68 9030 Z2 L24 Q69 9031 Z2 L24 Q70 9032 Z2 L24 Q71 9033 Z2 L24 Q72 9034 Z2 L24 Q73 9035 Z2 L24 Q74 9036 Z2 L24 Q75 9037 Z2 L24 Q76 9038 Z2 L24 Q77 9039 Z2 L24 Q78 9040 Z2 L24 Q79 9041 Z2 L24 Q80 9042 Z2 L24 Q81 9043 Z2 L24 Q82 9044 Z2 L24 Q83 9045 Z2 L24 Q84 9046 Z2 L24 Q85 9047 Z2 L24 Q86 9048 Z2 L24 Q87 9049 Z2 L24 Q88 9050 Z2 L24 Q89 9051 Z2 L24 Q90 9052 Z2 L24 Q91 9053 Z2 L24 Q92 9054 Z2 L24 Q93 9055 Z2 L24 Q94 9056 Z2 L24 Q95 9057 Z2 L24 Q96 9058 Z2 L24 Q97 9059 Z2 L24 Q98 9060 Z2 L24 Q99 9061 Z2 L24 Q100 9062 Z2 L24 Q101 9063 Z2 L24 Q102 9064 Z2 L24 Q103 9065 Z2 L25 Q1 9066 Z2 L25 Q2 9067 Z2 L25 Q3 9068 Z2 L25 Q4 9069 Z2 L25 Q5 9070 Z2 L25 Q6 9071 Z2 L25 Q7 9072 Z2 L25 Q8 9073 Z2 L25 Q9 9074 Z2 L25 Q10 9075 Z2 L25 Q11 9076 Z2 L25 Q12 9077 Z2 L25 Q13 9078 Z2 L25 Q14 9079 Z2 L25 Q15 9080 Z2 L25 Q16 9081 Z2 L25 Q17 9082 Z2 L25 Q18 9083 Z2 L25 Q19 9084 Z2 L25 Q20 9085 Z2 L25 Q21 9086 Z2 L25 Q22 9087 Z2 L25 Q23 9088 Z2 L25 Q24 9089 Z2 L25 Q25 9090 Z2 L25 Q26 9091 Z2 L25 Q27 9092 Z2 L25 Q28 9093 Z2 L25 Q29 9094 Z2 L25 Q30 9095 Z2 L25 Q31 9096 Z2 L25 Q32 9097 Z2 L25 Q33 9098 Z2 L25 Q34 9099 Z2 L25 Q35 9100 Z2 L25 Q36 9101 Z2 L25 Q37 9102 Z2 L25 Q38 9103 Z2 L25 Q39 9104 Z2 L25 Q40 9105 Z2 L25 Q41 9106 Z2 L25 Q42 9107 Z2 L25 Q43 9108 Z2 L25 Q44 9109 Z2 L25 Q45 9110 Z2 L25 Q46 9111 Z2 L25 Q47 9112 Z2 L25 Q48 9113 Z2 L25 Q49 9114 Z2 L25 Q50 9115 Z2 L25 Q51 9116 Z2 L25 Q52 9117 Z2 L25 Q53 9118 Z2 L25 Q54 9119 Z2 L25 Q55 9120 Z2 L25 Q56 9121 Z2 L25 Q57 9122 Z2 L25 Q58 9123 Z2 L25 Q59 9124 Z2 L25 Q60 9125 Z2 L25 Q61 9126 Z2 L25 Q62 9127 Z2 L25 Q63 9128 Z2 L25 Q64 9129 Z2 L25 Q65 9130 Z2 L25 Q66 9131 Z2 L25 Q67 9132 Z2 L25 Q68 9133 Z2 L25 Q69 9134 Z2 L25 Q70 9135 Z2 L25 Q71 9136 Z2 L25 Q72 9137 Z2 L25 Q73 9138 Z2 L25 Q74 9139 Z2 L25 Q75 9140 Z2 L25 Q76 9141 Z2 L25 Q77 9142 Z2 L25 Q78 9143 Z2 L25 Q79 9144 Z2 L25 Q80 9145 Z2 L25 Q81 9146 Z2 L25 Q82 9147 Z2 L25 Q83 9148 Z2 L25 Q84 9149 Z2 L25 Q85 9150 Z2 L25 Q86 9151 Z2 L25 Q87 9152 Z2 L25 Q88 9153 Z2 L25 Q89 9154 Z2 L25 Q90 9155 Z2 L25 Q91 9156 Z2 L25 Q92 9157 Z2 L25 Q93 9158 Z2 L25 Q94 9159 Z2 L25 Q95 9160 Z2 L25 Q96 9161 Z2 L25 Q97 9162 Z2 L25 Q98 9163 Z2 L25 Q99 9164 Z2 L25 Q100 9165 Z2 L25 Q101 9166 Z2 L25 Q102 9167 Z2 L25 Q103 9168 Z2 L26 Q1 9169 Z2 L26 Q2 9170 Z2 L26 Q3 9171 Z2 L26 Q4 9172 Z2 L26 Q5 9173 Z2 L26 Q6 9174 Z2 L26 Q7 9175 Z2 L26 Q8 9176 Z2 L26 Q9 9177 Z2 L26 Q10 9178 Z2 L26 Q11 9179 Z2 L26 Q12 9130 Z2 L26 Q13 9181 Z2 L26 Q14 9182 Z2 L26 Q15 9183 Z2 L26 Q16 9184 Z2 L26 Q17 9185 Z2 L26 Q18 9186 Z2 L26 Q19 9187 Z2 L26 Q20 9188 Z2 L26 Q21 9189 Z2 L26 Q22 9190 Z2 L26 Q23 9191 Z2 L26 Q24 9192 Z2 L26 Q25 9193 Z2 L26 Q26 9194 Z2 L26 Q27 9195 Z2 L26 Q28 9196 Z2 L26 Q29 9197 Z2 L26 Q30 9198 Z2 L26 Q31 9199 Z2 L26 Q32 9200 Z2 L26 Q33 9201 Z2 L26 Q34 9202 Z2 L26 Q35 9203 Z2 L26 Q36 9204 Z2 L26 Q37 9205 Z2 L26 Q38 9206 Z2 L26 Q39 9207 Z2 L26 Q40 9208 Z2 L26 Q41 9209 Z2 L26 Q42 9210 Z2 L26 Q43 9211 Z2 L26 Q44 9212 Z2 L26 Q45 9213 Z2 L26 Q46 9214 Z2 L26 Q47 9215 Z2 L26 Q48 9216 Z2 L26 Q49 9217 Z2 L26 Q50 9218 Z2 L26 Q51

TABLE 1-52 9219 Z2 L26 Q52 9220 Z2 L26 Q53 9221 Z2 L26 Q54 9222 Z2 L26 Q55 9223 Z2 L26 Q56 9224 Z2 L26 Q57 9225 Z2 L26 Q58 9226 Z2 L26 Q59 9227 Z2 L26 Q60 9228 Z2 L26 Q61 9229 Z2 L26 Q62 9230 Z2 L26 Q63 9231 Z2 L26 Q64 9232 Z2 L26 Q65 9233 Z2 L26 Q66 9234 Z2 L26 Q67 9235 Z2 L26 Q68 9236 Z2 L26 Q69 9237 Z2 L26 Q70 9238 Z2 L26 Q71 9239 Z2 L26 Q72 9240 Z2 L26 Q73 9241 Z2 L26 Q74 9242 Z2 L26 Q75 9243 Z2 L26 Q76 9244 Z2 L26 Q77 9245 Z2 L26 Q78 9246 Z2 L26 Q79 9247 Z2 L26 Q80 9248 Z2 L26 Q81 9249 Z2 L26 Q82 9250 Z2 L26 Q83 9251 Z2 L26 Q84 9252 Z2 L26 Q85 9253 Z2 L26 Q86 9254 Z2 L26 Q87 9255 Z2 L26 Q88 9256 Z2 L26 Q89 9257 Z2 L26 Q90 9258 Z2 L26 Q91 9259 Z2 L26 Q92 9260 Z2 L26 Q93 9261 Z2 L26 Q94 9262 Z2 L26 Q95 9263 Z2 L26 Q96 9264 Z2 L26 Q97 9265 Z2 L26 Q98 9266 Z2 L26 Q99 9267 Z2 L26 Q100 9268 Z2 L26 Q101 9269 Z2 L26 Q102 9270 Z2 L26 Q103 9271 Z2 L27 Q1 9272 Z2 L27 Q2 9273 Z2 L27 Q3 9274 Z2 L27 Q4 9275 Z2 L27 Q5 9276 Z2 L27 Q6 9277 Z2 L27 Q7 9278 Z2 L27 Q8 9279 Z2 L27 Q9 9280 Z2 L27 Q10 9281 Z2 L27 Q11 9282 Z2 L27 Q12 9283 Z2 L27 Q13 9284 Z2 L27 Q14 9285 Z2 L27 Q15 9286 Z2 L27 Q16 9287 Z2 L27 Q17 9288 Z2 L27 Q18 9289 Z2 L27 Q19 9290 Z2 L27 Q20 9291 Z2 L27 Q21 9292 Z2 L27 Q22 9293 Z2 L27 Q23 9294 Z2 L27 Q24 9295 Z2 L27 Q25 9296 Z2 L27 Q26 9297 Z2 L27 Q27 9298 Z2 L27 Q28 9299 Z2 L27 Q29 9300 Z2 L27 Q30 9301 Z2 L27 Q31 9302 Z2 L27 Q32 9303 Z2 L27 Q33 9304 Z2 L27 Q34 9305 Z2 L27 Q35 9306 Z2 L27 Q36 9307 Z2 L27 Q37 9308 Z2 L27 Q38 9309 Z2 L27 Q39 9310 Z2 L27 Q40 9311 Z2 L27 Q41 9312 Z2 L27 Q42 9313 Z2 L27 Q43 9314 Z2 L27 Q44 9315 Z2 L27 Q45 9316 Z2 L27 Q46 9317 Z2 L27 Q47 9318 Z2 L27 Q48 9319 Z2 L27 Q49 9320 Z2 L27 Q50 9321 Z2 L27 Q51 9322 Z2 L27 Q52 9323 Z2 L27 Q53 9324 Z2 L27 Q54 9325 Z2 L27 Q55 9326 Z2 L27 Q56 9327 Z2 L27 Q57 9328 Z2 L27 Q58 9329 Z2 L27 Q59 9330 Z2 L27 Q60 9331 Z2 L27 Q61 9332 Z2 L27 Q62 9333 Z2 L27 Q63 9334 Z2 L27 Q64 9335 Z2 L27 Q65 9336 Z2 L27 Q66 9337 Z2 L27 Q67 9338 Z2 L27 Q68 9339 Z2 L27 Q69 9340 Z2 L27 Q70 9341 Z2 L27 Q71 9342 Z2 L27 Q72 9343 Z2 L27 Q73 9344 Z2 L27 Q74 9345 Z2 L27 Q75 9346 Z2 L27 Q76 9347 Z2 L27 Q77 9348 Z2 L27 Q78 9349 Z2 L27 Q79 9350 Z2 L27 Q80 9351 Z2 L27 Q81 9352 Z2 L27 Q82 9353 Z2 L27 Q83 9354 Z2 L27 Q84 9355 Z2 L27 Q85 9356 Z2 L27 Q86 9357 Z2 L27 Q87 9358 Z2 L27 Q88 9359 Z2 L27 Q89 9360 Z2 L27 Q90 9361 Z2 L27 Q91 9362 Z2 L27 Q92 9363 Z2 L27 Q93 9364 Z2 L27 Q94 9365 Z2 L27 Q95 9366 Z2 L27 Q96 9367 Z2 L27 Q97 9368 Z2 L27 Q98 9369 Z2 L27 Q99 9370 Z2 L27 Q100 9371 Z2 L27 Q101 9372 Z2 L27 Q102 9373 Z2 L27 Q103 9374 Z2 L28 Q1 9375 Z2 L28 Q2 9376 Z2 L28 Q3 9377 Z2 L28 Q4 9378 Z2 L28 Q5 9379 Z2 L28 Q6 9380 Z2 L28 Q7 9381 Z2 L28 Q8 9382 Z2 L28 Q9 9383 Z2 L28 Q10 9384 Z2 L28 Q11 9385 Z2 L28 Q12 9386 Z2 L28 Q13 9387 Z2 L28 Q14 9388 Z2 L28 Q15 9389 Z2 L28 Q16 9390 Z2 L28 Q17 9391 Z2 L28 Q18 9392 Z2 L28 Q19 9393 Z2 L28 Q20 9394 Z2 L28 Q21 9395 Z2 L28 Q22 9396 Z2 L28 Q23 9397 Z2 L28 Q24 9398 Z2 L28 Q25 9399 Z2 L28 Q26 9400 Z2 L28 Q27 9401 Z2 L28 Q28 9402 Z2 L28 Q29 9403 Z2 L28 Q30 9404 Z2 L28 Q31 9405 Z2 L28 Q32 9406 Z2 L28 Q33 9407 Z2 L28 Q34 9408 Z2 L28 Q35 9409 Z2 L28 Q36 9410 Z2 L28 Q37 9411 Z2 L28 Q38 9412 Z2 L28 Q39 9413 Z2 L28 Q40 9414 Z2 L28 Q41 9415 Z2 L28 Q42 9416 Z2 L28 Q43 9417 Z2 L28 Q44 9418 Z2 L28 Q45 9419 Z2 L28 Q46

TABLE 1-53 9420 Z2 L28 Q47 9421 Z2 L28 Q48 9422 Z2 L28 Q49 9423 Z2 L28 Q50 9424 Z2 L28 Q51 9425 Z2 L28 Q52 9426 Z2 L28 Q53 9427 Z2 L28 Q54 9428 Z2 L28 Q55 9429 Z2 L28 Q56 9430 Z2 L28 Q57 9431 Z2 L28 Q58 9432 Z2 L28 Q59 9433 Z2 L28 Q60 9434 Z2 L28 Q61 9435 Z2 L28 Q62 9436 Z2 L28 Q63 9437 Z2 L28 Q64 9438 Z2 L28 Q65 9439 Z2 L28 Q66 9440 Z2 L28 Q67 9441 Z2 L28 Q68 9442 Z2 L28 Q69 9443 Z2 L28 Q70 9444 Z2 L28 Q71 9445 Z2 L28 Q72 9446 Z2 L28 Q73 9447 Z2 L28 Q74 9448 Z2 L28 Q75 9449 Z2 L28 Q76 9450 Z2 L28 Q77 9451 Z2 L28 Q78 9452 Z2 L28 Q79 9453 Z2 L28 Q80 9454 Z2 L28 Q81 9455 Z2 L28 Q82 9456 Z2 L28 Q83 9457 Z2 L28 Q84 9458 Z2 L28 Q85 9459 Z2 L28 Q86 9460 Z2 L28 Q87 9461 Z2 L28 Q88 9462 Z2 L28 Q89 9463 Z2 L28 Q90 9464 Z2 L28 Q91 9465 Z2 L28 Q92 9466 Z2 L28 Q93 9467 Z2 L28 Q94 9468 Z2 L28 Q95 9469 Z2 L28 Q96 9470 Z2 L28 Q97 9471 Z2 L28 Q98 9472 Z2 L28 Q99 9473 Z2 L28 Q100 9474 Z2 L28 Q101 9475 Z2 L28 Q102 9476 Z2 L28 Q103 9477 Z2 L29 Q1 9478 Z2 L29 Q2 9479 Z2 L29 Q3 9480 Z2 L29 Q4 9481 Z2 L29 Q5 9482 Z2 L29 Q6 9483 Z2 L29 Q7 9484 Z2 L29 Q8 9485 Z2 L29 Q9 9486 Z2 L29 Q10 9487 Z2 L29 Q11 9488 Z2 L29 Q12 9489 Z2 L29 Q13 9490 Z2 L29 Q14 9491 Z2 L29 Q15 9492 Z2 L29 Q16 9493 Z2 L29 Q17 9494 Z2 L29 Q18 9495 Z2 L29 Q19 9496 Z2 L29 Q20 9497 Z2 L29 Q21 9498 Z2 L29 Q22 9499 Z2 L29 Q23 9500 Z2 L29 Q24 9501 Z2 L29 Q25 9502 Z2 L29 Q26 9503 Z2 L29 Q27 9504 Z2 L29 Q28 9505 Z2 L29 Q29 9506 Z2 L29 Q30 9507 Z2 L29 Q31 9508 Z2 L29 Q32 9509 Z2 L29 Q33 9510 Z2 L29 Q34 9511 Z2 L29 Q35 9512 Z2 L29 Q36 9513 Z2 L29 Q37 9514 Z2 L29 Q38 9515 Z2 L29 Q39 9516 Z2 L29 Q40 9517 Z2 L29 Q41 9518 Z2 L29 Q42 9519 Z2 L29 Q43 9520 Z2 L29 Q44 9521 Z2 L29 Q45 9522 Z2 L29 Q46 9523 Z2 L29 Q47 9524 Z2 L29 Q48 9525 Z2 L29 Q49 9526 Z2 L29 Q50 9527 Z2 L29 Q51 9528 Z2 L29 Q52 9529 Z2 L29 Q53 9530 Z2 L29 Q54 9531 Z2 L29 Q55 9532 Z2 L29 Q56 9533 Z2 L29 Q57 9534 Z2 L29 Q58 9535 Z2 L29 Q59 9536 Z2 L29 Q60 9537 Z2 L29 Q61 9538 Z2 L29 Q62 9539 Z2 L29 Q63 9540 Z2 L29 Q64 9541 Z2 L29 Q65 9542 Z2 L29 Q66 9543 Z2 L29 Q67 9544 Z2 L29 Q68 9545 Z2 L29 Q69 9546 Z2 L29 Q70 9547 Z2 L29 Q71 9548 Z2 L29 Q72 9549 Z2 L29 Q73 9550 Z2 L29 Q74 9551 Z2 L29 Q75 9552 Z2 L29 Q76 9553 Z2 L29 Q77 9554 Z2 L29 Q78 9555 Z2 L29 Q79 9556 Z2 L29 Q80 9557 Z2 L29 Q81 9558 Z2 L29 Q82 9559 Z2 L29 Q83 9560 Z2 L29 Q84 9561 Z2 L29 Q85 9562 Z2 L29 Q86 9563 Z2 L29 Q87 9564 Z2 L29 Q88 9565 Z2 L29 Q89 9566 Z2 L29 Q90 9567 Z2 L29 Q91 9568 Z2 L29 Q92 9569 Z2 L29 Q93 9570 Z2 L29 Q94 9571 Z2 L29 Q95 9572 Z2 L29 Q96 9573 Z2 L29 Q97 9574 Z2 L29 Q98 9575 Z2 L29 Q99 9576 Z2 L29 Q100 9577 Z2 L29 Q101 9578 Z2 L29 Q102 9579 Z2 L29 Q103 9580 Z2 L30 Q1 9581 Z2 L30 Q2 9582 Z2 L30 Q3 9583 Z2 L30 Q4 9584 Z2 L30 Q5 9585 Z2 L30 Q6 9586 Z2 L30 Q7 9587 Z2 L30 Q8 9588 Z2 L30 Q9 9589 Z2 L30 Q10 9590 Z2 L30 Q11 9591 Z2 L30 Q12 9592 Z2 L30 Q13 9593 Z2 L30 Q14 9594 Z2 L30 Q15 9595 Z2 L30 Q16 9596 Z2 L30 Q17 9597 Z2 L30 Q18 9598 Z2 L30 Q19 9599 Z2 L30 Q20 9600 Z2 L30 Q21 9601 Z2 L30 Q22 9602 Z2 L30 Q23 9603 Z2 L30 Q24 9604 Z2 L30 Q25 9605 Z2 L30 Q26 9606 Z2 L30 Q27 9607 Z2 L30 Q28 9608 Z2 L30 Q29 9609 Z2 L30 Q30 9610 Z2 L30 Q31 9611 Z2 L30 Q32 9612 Z2 L30 Q33 9613 Z2 L30 Q34 9614 Z2 L30 Q35 9615 Z2 L30 Q36 9616 Z2 L30 Q37 9617 Z2 L30 Q38 9618 Z2 L30 Q39 9619 Z2 L30 Q40 9620 Z2 L30 Q41

TABLE 1-54 9621 Z2 L30 Q42 9622 Z2 L30 Q43 9623 Z2 L30 Q44 9624 Z2 L30 Q45 9625 Z2 L30 Q46 9626 Z2 L30 Q47 9627 Z2 L30 Q48 9628 Z2 L30 Q49 9629 Z2 L30 Q50 9630 Z2 L30 Q51 9631 Z2 L30 Q52 9632 Z2 L30 Q53 9633 Z2 L30 Q54 9634 Z2 L30 Q55 9635 Z2 L30 Q56 9636 Z2 L30 Q57 9637 Z2 L30 Q58 9638 Z2 L30 Q59 9639 Z2 L30 Q60 9640 Z2 L30 Q61 9641 Z2 L30 Q62 9642 Z2 L30 Q63 9643 Z2 L30 Q64 9644 Z2 L30 Q65 9645 Z2 L30 Q66 9646 Z2 L30 Q67 9647 Z2 L30 Q68 9648 Z2 L30 Q69 9649 Z2 L30 Q70 9650 Z2 L30 Q71 9651 Z2 L30 Q72 9652 Z2 L30 Q73 9653 Z2 L30 Q74 9654 Z2 L30 Q75 9655 Z2 L30 Q76 9656 Z2 L30 Q77 9657 Z2 L30 Q78 9658 Z2 L30 Q79 9659 Z2 L30 Q80 9660 Z2 L30 Q81 9661 Z2 L30 Q82 9662 Z2 L30 Q83 9663 Z2 L30 Q84 9664 Z2 L30 Q85 9665 Z2 L30 Q86 9666 Z2 L30 Q87 9667 Z2 L30 Q88 9668 Z2 L30 Q89 9669 Z2 L30 Q90 9670 Z2 L30 Q91 9671 Z2 L30 Q92 9672 Z2 L30 Q93 9673 Z2 L30 Q94 9674 Z2 L30 Q95 9675 Z2 L30 Q96 9676 Z2 L30 Q97 9677 Z2 L30 Q98 9678 Z2 L30 Q99 9679 Z2 L30 Q100 9680 Z2 L30 Q101 9681 Z2 L30 Q102 9682 Z2 L30 Q103 9683 Z2 L31 Q1 9684 Z2 L31 Q2 9685 Z2 L31 Q3 9686 Z2 L31 Q4 9687 Z2 L31 Q5 9688 Z2 L31 Q6 9689 Z2 L31 Q7 9690 Z2 L31 Q8 9691 Z2 L31 Q9 9692 Z2 L31 Q10 9693 Z2 L31 Q11 9694 Z2 L31 Q12 9695 Z2 L31 Q13 9696 Z2 L31 Q14 9697 Z2 L31 Q15 9698 Z2 L31 Q16 9699 Z2 L31 Q17 9700 Z2 L31 Q18 9701 Z2 L31 Q19 9702 Z2 L31 Q20 9703 Z2 L31 Q21 9704 Z2 L31 Q22 9705 Z2 L31 Q23 9706 Z2 L31 Q24 9707 Z2 L31 Q25 9708 Z2 L31 Q26 9709 Z2 L31 Q27 9710 Z2 L31 Q28 9711 Z2 L31 Q29 9712 Z2 L31 Q30 9713 Z2 L31 Q31 9714 Z2 L31 Q32 9715 Z2 L31 Q33 9716 Z2 L31 Q34 9717 Z2 L31 Q35 9718 Z2 L31 Q36 9719 Z2 L31 Q37 9720 Z2 L31 Q38 9721 Z2 L31 Q39 9722 Z2 L31 Q40 9723 Z2 L31 Q41 9724 Z2 L31 Q42 9725 Z2 L31 Q43 9726 Z2 L31 Q44 9727 Z2 L31 Q45 9728 Z2 L31 Q46 9729 Z2 L31 Q47 9730 Z2 L31 Q48 9731 Z2 L31 Q49 9732 Z2 L31 Q50 9733 Z2 L31 Q51 9734 Z2 L31 Q52 9735 Z2 L31 Q53 9736 Z2 L31 Q54 9737 Z2 L31 Q55 9738 Z2 L31 Q56 9739 Z2 L31 Q57 9740 Z2 L31 Q58 9741 Z2 L31 Q59 9742 Z2 L31 Q60 9743 Z2 L31 Q61 9744 Z2 L31 Q62 9745 Z2 L31 Q63 9746 Z2 L31 Q64 9747 Z2 L31 Q65 9748 Z2 L31 Q66 9749 Z2 L31 Q67 9750 Z2 L31 Q68 9751 Z2 L31 Q69 9752 Z2 L31 Q70 9753 Z2 L31 Q71 9754 Z2 L31 Q72 9755 Z2 L31 Q73 9756 Z2 L31 Q74 9757 Z2 L31 Q75 9758 Z2 L31 Q76 9759 Z2 L31 Q77 9760 Z2 L31 Q78 9761 Z2 L31 Q79 9762 Z2 L31 Q80 9763 Z2 L31 Q81 9764 Z2 L31 Q82 9765 Z2 L31 Q83 9766 Z2 L31 Q84 9767 Z2 L31 Q85 9768 Z2 L31 Q86 9769 Z2 L31 Q87 9770 Z2 L31 Q88 9771 Z2 L31 Q89 9772 Z2 L31 Q90 9773 Z2 L31 Q91 9774 Z2 L31 Q92 9775 Z2 L31 Q93 9776 Z2 L31 Q94 9777 Z2 L31 Q95 9778 Z2 L31 Q96 9779 Z2 L31 Q97 9780 Z2 L31 Q98 9781 Z2 L31 Q99 9782 Z2 L31 Q100 9783 Z2 L31 Q101 9784 Z2 L31 Q102 9785 Z2 L31 Q103 9786 Z2 L32 Q1 9787 Z2 L32 Q2 9788 Z2 L32 Q3 9789 Z2 L32 Q4 9790 Z2 L32 Q5 9791 Z2 L32 Q6 9792 Z2 L32 Q7 9793 Z2 L32 Q8 9794 Z2 L32 Q9 9795 Z2 L32 Q10 9796 Z2 L32 Q11 9797 Z2 L32 Q12 9798 Z2 L32 Q13 9799 Z2 L32 Q14 9800 Z2 L32 Q15 9801 Z2 L32 Q16 9802 Z2 L32 Q17 9803 Z2 L32 Q18 9804 Z2 L32 Q19 9805 Z2 L32 Q20 9806 Z2 L32 Q21 9807 Z2 L32 Q22 9808 Z2 L32 Q23 9809 Z2 L32 Q24 9810 Z2 L32 Q25 9811 Z2 L32 Q26 9812 Z2 L32 Q27 9813 Z2 L32 Q28 9814 Z2 L32 Q29 9815 Z2 L32 Q30 9816 Z2 L32 Q31 9817 Z2 L32 Q32 9818 Z2 L32 Q33 9819 Z2 L32 Q34 9820 Z2 L32 Q35 9821 Z2 L32 Q36

TABLE 1-55 9822 Z2 L32 Q37 9823 Z2 L32 Q38 9824 Z2 L32 Q39 9825 Z2 L32 Q40 9826 Z2 L32 Q41 9827 Z2 L32 Q42 9828 Z2 L32 Q43 9829 Z2 L32 Q44 9830 Z2 L32 Q45 9831 Z2 L32 Q46 9832 Z2 L32 Q47 9833 Z2 L32 Q48 9834 Z2 L32 Q49 9835 Z2 L32 Q50 9836 Z2 L32 Q51 9837 Z2 L32 Q52 9838 Z2 L32 Q53 9839 Z2 L32 Q54 9840 Z2 L32 Q55 9841 Z2 L32 Q56 9842 Z2 L32 Q57 9843 Z2 L32 Q58 9844 Z2 L32 Q59 9845 Z2 L32 Q60 9846 Z2 L32 Q61 9847 Z2 L32 Q62 9848 Z2 L32 Q63 9849 Z2 L32 Q64 9850 Z2 L32 Q65 9851 Z2 L32 Q66 9852 Z2 L32 Q67 9853 Z2 L32 Q68 9854 Z2 L32 Q69 9855 Z2 L32 Q70 9856 Z2 L32 Q71 9857 Z2 L32 Q72 9858 Z2 L32 Q73 9859 Z2 L32 Q74 9860 Z2 L32 Q75 9861 Z2 L32 Q76 9862 Z2 L32 Q77 9863 Z2 L32 Q78 9864 Z2 L32 Q79 9865 Z2 L32 Q80 9866 Z2 L32 Q81 9867 Z2 L32 Q82 9868 Z2 L32 Q83 9869 Z2 L32 Q84 9870 Z2 L32 Q85 9871 Z2 L32 Q86 9872 Z2 L32 Q87 9873 Z2 L32 Q88 9874 Z2 L32 Q89 9875 Z2 L32 Q90 9876 Z2 L32 Q91 9877 Z2 L32 Q92 9878 Z2 L32 Q93 9879 Z2 L32 Q94 9880 Z2 L32 Q95 9881 Z2 L32 Q96 9882 Z2 L32 Q97 9883 Z2 L32 Q98 9884 Z2 L32 Q99 9885 Z2 L32 Q100 9886 Z2 L32 Q101 9887 Z2 L32 Q102 9888 Z2 L32 Q103 9889 Z2 L33 Q1 9890 Z2 L33 Q2 9891 Z2 L33 Q3 9892 Z2 L33 Q4 9893 Z2 L33 Q5 9894 Z2 L33 Q6 9895 Z2 L33 Q7 9896 Z2 L33 Q8 9897 Z2 L33 Q9 9898 Z2 L33 Q10 9899 Z2 L33 Q11 9900 Z2 L33 Q12 9901 Z2 L33 Q13 9902 Z2 L33 Q14 9903 Z2 L33 Q15 9904 Z2 L33 Q16 9905 Z2 L33 Q17 9906 Z2 L33 Q18 9907 Z2 L33 Q19 9908 Z2 L33 Q20 9909 Z2 L33 Q21 9910 Z2 L33 Q22 9911 Z2 L33 Q23 9912 Z2 L33 Q24 9913 Z2 L33 Q25 9914 Z2 L33 Q26 9915 Z2 L33 Q27 9916 Z2 L33 Q28 9917 Z2 L33 Q29 9918 Z2 L33 Q30 9919 Z2 L33 Q31 9920 Z2 L33 Q32 9921 Z2 L33 Q33 9922 Z2 L33 Q34 9923 Z2 L33 Q35 9924 Z2 L33 Q36 9925 Z2 L33 Q37 9926 Z2 L33 Q38 9927 Z2 L33 Q39 9928 Z2 L33 Q40 9929 Z2 L33 Q41 9930 Z2 L33 Q42 9931 Z2 L33 Q43 9932 Z2 L33 Q44 9933 Z2 L33 Q45 9934 Z2 L33 Q46 9935 Z2 L33 Q47 9936 Z2 L33 Q48 9937 Z2 L33 Q49 9938 Z2 L33 Q50 9939 Z2 L33 Q51 9940 Z2 L33 Q52 9941 Z2 L33 Q53 9942 Z2 L33 Q54 9943 Z2 L33 Q55 9944 Z2 L33 Q56 9945 Z2 L33 Q57 9946 Z2 L33 Q58 9947 Z2 L33 Q59 9948 Z2 L33 Q60 9949 Z2 L33 Q61 9950 Z2 L33 Q62 9951 Z2 L33 Q63 9952 Z2 L33 Q64 9953 Z2 L33 Q65 9954 Z2 L33 Q66 9955 Z2 L33 Q67 9956 Z2 L33 Q68 9957 Z2 L33 Q69 9958 Z2 L33 Q70 9959 Z2 L33 Q71 9960 Z2 L33 Q72 9961 Z2 L33 Q73 9962 Z2 L33 Q74 9963 Z2 L33 Q75 9964 Z2 L33 Q76 9965 Z2 L33 Q77 9966 Z2 L33 Q78 9967 Z2 L33 Q79 9968 Z2 L33 Q80 9969 Z2 L33 Q81 9970 Z2 L33 Q82 9971 Z2 L33 Q83 9972 Z2 L33 Q84 9973 Z2 L33 Q85 9974 Z2 L33 Q86 9975 Z2 L33 Q87 9976 Z2 L33 Q88 9977 Z2 L33 Q89 9978 Z2 L33 Q90 9979 Z2 L33 Q91 9980 Z2 L33 Q92 9981 Z2 L33 Q93 9982 Z2 L33 Q94 9983 Z2 L33 Q95 9984 Z2 L33 Q96 9985 Z2 L33 Q97 9986 Z2 L33 Q98 9987 Z2 L33 Q99 9988 Z2 L33 Q100 9989 Z2 L33 Q101 9990 Z2 L33 Q102 9991 Z2 L33 Q103 9992 Z2 L34 Q1 9993 Z2 L34 Q2 9994 Z2 L34 Q3 9995 Z2 L34 Q4 9996 Z2 L34 Q5 9997 Z2 L34 Q6 9998 Z2 L34 Q7 9999 Z2 L34 Q8 10000 Z2 L34 Q9 10001 Z2 L34 Q10 10002 Z2 L34 Q11 10003 Z2 L34 Q12 10004 Z2 L34 Q13 10005 Z2 L34 Q14 10006 Z2 L34 Q15 10007 Z2 L34 Q16 10008 Z2 L34 Q17 10009 Z2 L34 Q18 10010 Z2 L34 Q19 10011 Z2 L34 Q20 10012 Z2 L34 Q21 10013 Z2 L34 Q22 10014 Z2 L34 Q23 10015 Z2 L34 Q24 10016 Z2 L34 Q25 10017 Z2 L34 Q26 10018 Z2 L34 Q27 10019 Z2 L34 Q28 10020 Z2 L34 Q29 10021 Z2 L34 Q30 10022 Z2 L34 Q31

TABLE 1-56 10023 Z2 L34 Q32 10024 Z2 L34 Q33 10025 Z2 L34 Q34 10026 Z2 L34 Q35 10027 Z2 L34 Q36 10028 Z2 L34 Q37 10029 Z2 L34 Q38 10030 Z2 L34 Q39 10031 Z2 L34 Q40 10032 Z2 L34 Q41 10033 Z2 L34 Q42 10034 Z2 L34 Q43 10035 Z2 L34 Q44 10036 Z2 L34 Q45 10037 Z2 L34 Q46 10038 Z2 L34 Q47 10039 Z2 L34 Q48 10040 Z2 L34 Q49 10041 Z2 L34 Q50 10042 Z2 L34 Q51 10043 Z2 L34 Q52 10044 Z2 L34 Q53 10045 Z2 L34 Q54 10046 Z2 L34 Q55 10047 Z2 L34 Q56 10048 Z2 L34 Q57 10049 Z2 L34 Q58 10050 Z2 L34 Q59 10051 Z2 L34 Q60 10052 Z2 L34 Q61 10053 Z2 L34 Q62 10054 Z2 L34 Q63 10055 Z2 L34 Q64 10056 Z2 L34 Q65 10057 Z2 L34 Q66 10058 Z2 L34 Q67 10059 Z2 L34 Q68 10060 Z2 L34 Q69 10061 Z2 L34 Q70 10062 Z2 L34 Q71 10063 Z2 L34 Q72 10064 Z2 L34 Q73 10065 Z2 L34 Q74 10066 Z2 L34 Q75 10067 Z2 L34 Q76 10068 Z2 L34 Q77 10069 Z2 L34 Q78 10070 Z2 L34 Q79 10071 Z2 L34 Q80 10072 Z2 L34 Q81 10073 Z2 L34 Q82 10074 Z2 L34 Q83 10075 Z2 L34 Q84 10076 Z2 L34 Q85 10077 Z2 L34 Q86 10078 Z2 L34 Q87 10079 Z2 L34 Q88 10080 Z2 L34 Q89 10081 Z2 L34 Q90 10082 Z2 L34 Q91 10083 Z2 L34 Q92 10084 Z2 L34 Q93 10085 Z2 L34 Q94 10086 Z2 L34 Q95 10087 Z2 L34 Q96 10088 Z2 L34 Q97 10089 Z2 L34 Q98 10090 Z2 L34 Q99 10091 Z2 L34 Q100 10092 Z2 L34 Q101 10093 Z2 L34 Q102 10094 Z2 L34 Q103 10095 Z2 L35 Q1 10096 Z2 L35 Q2 10097 Z2 L35 Q3 10098 Z2 L35 Q4 10099 Z2 L35 Q5 10100 Z2 L35 Q6 10101 Z2 L35 Q7 10102 Z2 L35 Q8 10103 Z2 L35 Q9 10104 Z2 L35 Q10 10105 Z2 L35 Q11 10106 Z2 L35 Q12 10107 Z2 L35 Q13 10108 Z2 L35 Q14 10109 Z2 L35 Q15 10110 Z2 L35 Q16 10111 Z2 L35 Q17 10112 Z2 L35 Q18 10113 Z2 L35 Q19 10114 Z2 L35 Q20 10115 Z2 L35 Q21 10116 Z2 L35 Q22 10117 Z2 L35 Q23 10118 Z2 L35 Q24 10119 Z2 L35 Q25 10120 Z2 L35 Q26 10121 Z2 L35 Q27 10122 Z2 L35 Q28 10123 Z2 L35 Q29 10124 Z2 L35 Q30 10125 Z2 L35 Q31 10126 Z2 L35 Q32 10127 Z2 L35 Q33 10128 Z2 L35 Q34 10129 Z2 L35 Q35 10130 Z2 L35 Q36 10131 Z2 L35 Q37 10132 Z2 L35 Q38 10133 Z2 L35 Q39 10134 Z2 L35 Q40 10135 Z2 L35 Q41 10136 Z2 L35 Q42 10137 Z2 L35 Q43 10138 Z2 L35 Q44 10139 Z2 L35 Q45 10140 Z2 L35 Q46 10141 Z2 L35 Q47 10142 Z2 L35 Q48 10143 Z2 L35 Q49 10144 Z2 L35 Q50 10145 Z2 L35 Q51 10146 Z2 L35 Q52 10147 Z2 L35 Q53 10148 Z2 L35 Q54 10149 Z2 L35 Q55 10150 Z2 L35 Q56 10151 Z2 L35 Q57 10152 Z2 L35 Q58 10153 Z2 L35 Q59 10154 Z2 L35 Q60 10155 Z2 L35 Q61 10156 Z2 L35 Q62 10157 Z2 L35 Q63 10158 Z2 L35 Q64 10159 Z2 L35 Q65 10160 Z2 L35 Q66 10161 Z2 L35 Q67 10162 Z2 L35 Q68 10163 Z2 L35 Q69 10164 Z2 L35 Q70 10165 Z2 L35 Q71 10166 Z2 L35 Q72 10167 Z2 L35 Q73 10168 Z2 L35 Q74 10169 Z2 L35 Q75 10170 Z2 L35 Q76 10171 Z2 L35 Q77 10172 Z2 L35 Q78 10173 Z2 L35 Q79 10174 Z2 L35 Q80 10175 Z2 L35 Q81 10176 Z2 L35 Q82 10177 Z2 L35 Q83 10178 Z2 L35 Q84 10179 Z2 L35 Q85 10180 Z2 L35 Q86 10181 Z2 L35 Q87 10182 Z2 L35 Q88 10183 Z2 L35 Q89 10184 Z2 L35 Q90 10185 Z2 L35 Q91 10186 Z2 L35 Q92 10187 Z2 L35 Q93 10188 Z2 L35 Q94 10189 Z2 L35 Q95 10190 Z2 L35 Q96 10191 Z2 L35 Q97 10192 Z2 L35 Q98 10193 Z2 L35 Q99 10194 Z2 L35 Q100 10195 Z2 L35 Q101 10196 Z2 L35 Q102 10197 Z2 L35 Q103 10198 Z2 L36 Q1 10199 Z2 L36 Q2 10200 Z2 L36 Q3 10201 Z2 L36 Q4 10202 Z2 L36 Q5 10203 Z2 L36 Q6 10204 Z2 L36 Q7 10205 Z2 L36 Q8 10206 Z2 L36 Q9 10207 Z2 L36 Q10 10208 Z2 L36 Q11 10209 Z2 L36 Q12 10210 Z2 L36 Q13 10211 Z2 L36 Q14 10212 Z2 L36 Q15 10213 Z2 L36 Q16 10214 Z2 L36 Q17 10215 Z2 L36 Q18 10216 Z2 L36 Q19 10217 Z2 L36 Q20 10218 Z2 L36 Q21 10219 Z2 L36 Q22 10220 Z2 L36 Q23 10221 Z2 L36 Q24 10222 Z2 L36 Q25 10223 Z2 L36 Q26

TABLE 1-57 10224 Z2 L36 Q27 10225 Z2 L36 Q28 10226 Z2 L36 Q29 10227 Z2 L36 Q30 10228 Z2 L36 Q31 10229 Z2 L36 Q32 10230 Z2 L36 Q33 10231 Z2 L36 Q34 10232 Z2 L36 Q35 10233 Z2 L36 Q36 10234 Z2 L36 Q37 10235 Z2 L36 Q38 10236 Z2 L36 Q39 10237 Z2 L36 Q40 10238 Z2 L36 Q41 10239 Z2 L36 Q42 10240 Z2 L36 Q43 10241 Z2 L36 Q44 10242 Z2 L36 Q45 10243 Z2 L36 Q46 10244 Z2 L36 Q47 10245 Z2 L36 Q48 10246 Z2 L36 Q49 10247 Z2 L36 Q50 10248 Z2 L36 Q51 10249 Z2 L36 Q52 10250 Z2 L36 Q53 10251 Z2 L36 Q54 10252 Z2 L36 Q55 10253 Z2 L36 Q56 10254 Z2 L36 Q57 10255 Z2 L36 Q58 10256 Z2 L36 Q59 10257 Z2 L36 Q60 10258 Z2 L36 Q61 10259 Z2 L36 Q62 10260 Z2 L36 Q63 10261 Z2 L36 Q64 10262 Z2 L36 Q65 10263 Z2 L36 Q66 10264 Z2 L36 Q67 10265 Z2 L36 Q68 10266 Z2 L36 Q69 10267 Z2 L36 Q70 10268 Z2 L36 Q71 10269 Z2 L36 Q72 10270 Z2 L36 Q73 10271 Z2 L36 Q74 10272 Z2 L36 Q75 10273 Z2 L36 Q76 10274 Z2 L36 Q77 10275 Z2 L36 Q78 10276 Z2 L36 Q79 10277 Z2 L36 Q80 10278 Z2 L36 Q81 10279 Z2 L36 Q82 10280 Z2 L36 Q83 10281 Z2 L36 Q84 10282 Z2 L36 Q85 10283 Z2 L36 Q86 10284 Z2 L36 Q87 10285 Z2 L36 Q88 10286 Z2 L36 Q89 10287 Z2 L36 Q90 10288 Z2 L36 Q91 10289 Z2 L36 Q92 10290 Z2 L36 Q93 10291 Z2 L36 Q94 10292 Z2 L36 Q95 10293 Z2 L36 Q96 10294 Z2 L36 Q97 10295 Z2 L36 Q98 10296 Z2 L36 Q99 10297 Z2 L36 Q100 10298 Z2 L36 Q101 10299 Z2 L36 Q102 10300 Z2 L36 Q103 10301 Z3 L15 Q1 10302 Z3 L15 Q2 10303 Z3 L15 Q3 10304 Z3 L15 Q4 10305 Z3 L15 Q5 10306 Z3 L15 Q6 10307 Z3 L15 Q7 10308 Z3 L15 Q8 10309 Z3 L15 Q9 10310 Z3 L15 Q10 10311 Z3 L15 Q11 10312 Z3 L15 Q12 10313 Z3 L15 Q13 10314 Z3 L15 Q14 10315 Z3 L15 Q15 10316 Z3 L15 Q16 10317 Z3 L15 Q17 10318 Z3 L15 Q18 10319 Z3 L15 Q19 10320 Z3 L15 Q20 10321 Z3 L15 Q21 10322 Z3 L15 Q22 10323 Z3 L15 Q23 10324 Z3 L15 Q24 10325 Z3 L15 Q25 10326 Z3 L15 Q26 10327 Z3 L15 Q27 10328 Z3 L15 Q28 10329 Z3 L15 Q29 10330 Z3 L15 Q30 10331 Z3 L15 Q31 10332 Z3 L15 Q32 10333 Z3 L15 Q33 10334 Z3 L15 Q34 10335 Z3 L15 Q35 10336 Z3 L15 Q36 10337 Z3 L15 Q37 10338 Z3 L15 Q38 10339 Z3 L15 Q39 10340 Z3 L15 Q40 10341 Z3 L15 Q41 10342 Z3 L15 Q42 10343 Z3 L15 Q43 10344 Z3 L15 Q44 10345 Z3 L15 Q45 10346 Z3 L15 Q46 10347 Z3 L15 Q47 10348 Z3 L15 Q48 10349 Z3 L15 Q49 10350 Z3 L15 Q50 10351 Z3 L15 Q51 10352 Z3 L15 Q52 10353 Z3 L15 Q53 10354 Z3 L15 Q54 10355 Z3 L15 Q55 10356 Z3 L15 Q56 10357 Z3 L15 Q57 10358 Z3 L15 Q58 10359 Z3 L15 Q59 10360 Z3 L15 Q60 10361 Z3 L15 Q61 10362 Z3 L15 Q62 10363 Z3 L15 Q63 10364 Z3 L15 Q64 10365 Z3 L15 Q65 10366 Z3 L15 Q66 10367 Z3 L15 Q67 10368 Z3 L15 Q68 10369 Z3 L15 Q69 10370 Z3 L15 Q70 10371 Z3 L15 Q71 10372 Z3 L15 Q72 10373 Z3 L15 Q73 10374 Z3 L15 Q74 10375 Z3 L15 Q75 10376 Z3 L15 Q76 10377 Z3 L15 Q77 10378 Z3 L15 Q78 10379 Z3 L15 Q79 10380 Z3 L15 Q80 10381 Z3 L15 Q81 10382 Z3 L15 Q82 10383 Z3 L15 Q83 10384 Z3 L15 Q84 10385 Z3 L15 Q85 10386 Z3 L15 Q86 10387 Z3 L15 Q87 10388 Z3 L15 Q88 10389 Z3 L15 Q89 10390 Z3 L15 Q90 10391 Z3 L15 Q91 10392 Z3 L15 Q92 10393 Z3 L15 Q93 10394 Z3 L15 Q94 10395 Z3 L15 Q95 10396 Z3 L15 Q96 10397 Z3 L15 Q97 10398 Z3 L15 Q98 10399 Z3 L15 Q99 10400 Z3 L15 Q100 10401 Z3 L15 Q101 10402 Z3 L15 Q102 10403 Z3 L15 Q103 10404 Z3 L16 Q1 10405 Z3 L16 Q2 10406 Z3 L16 Q3 10407 Z3 L16 Q4 10408 Z3 L16 Q5 10409 Z3 L16 Q6 10410 Z3 L16 Q7 10411 Z3 L16 Q8 10412 Z3 L16 Q9 10413 Z3 L16 Q10 10414 Z3 L16 Q11 10415 Z3 L16 Q12 10416 Z3 L16 Q13 10417 Z3 L16 Q14 10418 Z3 L16 Q15 10419 Z3 L16 Q16 10420 Z3 L16 Q17 10421 Z3 L16 Q18 10422 Z3 L16 Q19 10423 Z3 L16 Q20 10424 Z3 L16 Q21

TABLE 1-58 10425 Z3 L16 Q22 10426 Z3 L16 Q23 10427 Z3 L16 Q24 10428 Z3 L16 Q25 10429 Z3 L16 Q26 10430 Z3 L16 Q27 10431 Z3 L16 Q28 10432 Z3 L16 Q29 10433 Z3 L16 Q30 10434 Z3 L16 Q31 10435 Z3 L16 Q32 10436 Z3 L16 Q33 10437 Z3 L16 Q34 10438 Z3 L16 Q35 10439 Z3 L16 Q36 10440 Z3 L16 Q37 10441 Z3 L16 Q38 10442 Z3 L16 Q39 10443 Z3 L16 Q40 10444 Z3 L16 Q41 10445 Z3 L16 Q42 10446 Z3 L16 Q43 10447 Z3 L16 Q44 10448 Z3 L16 Q45 10449 Z3 L16 Q46 10450 Z3 L16 Q47 10451 Z3 L16 Q48 10452 Z3 L16 Q49 10453 Z3 L16 Q50 10454 Z3 L16 Q51 10455 Z3 L16 Q52 10456 Z3 L16 Q53 10457 Z3 L16 Q54 10458 Z3 L16 Q55 10459 Z3 L16 Q56 10460 Z3 L16 Q57 10461 Z3 L16 Q58 10462 Z3 L16 Q59 10463 Z3 L16 Q60 10464 Z3 L16 Q61 10465 Z3 L16 Q62 10466 Z3 L16 Q63 10467 Z3 L16 Q64 10468 Z3 L16 Q65 10469 Z3 L16 Q66 10470 Z3 L16 Q67 10471 Z3 L16 Q68 10472 Z3 L16 Q69 10473 Z3 L16 Q70 10474 Z3 L16 Q71 10475 Z3 L16 Q72 10476 Z3 L16 Q73 10477 Z3 L16 Q74 10478 Z3 L16 Q75 10479 Z3 L16 Q76 10480 Z3 L16 Q77 10481 Z3 L16 Q78 10482 Z3 L16 Q79 10483 Z3 L16 Q80 10484 Z3 L16 Q81 10485 Z3 L16 Q82 10486 Z3 L16 Q83 10487 Z3 L16 Q84 10488 Z3 L16 Q85 10489 Z3 L16 Q86 10490 Z3 L16 Q87 10491 Z3 L16 Q88 10492 Z3 L16 Q89 10493 Z3 L16 Q90 10494 Z3 L16 Q91 10495 Z3 L16 Q92 10496 Z3 L16 Q93 10497 Z3 L16 Q94 10498 Z3 L16 Q95 10499 Z3 L16 Q96 10500 Z3 L16 Q97 10501 Z3 L16 Q98 10502 Z3 L16 Q99 10503 Z3 L16 Q100 10504 Z3 L16 Q101 10505 Z3 L16 Q102 10506 Z3 L16 Q103 10507 Z3 L17 Q1 10508 Z3 L17 Q2 10509 Z3 L17 Q3 10510 Z3 L17 Q4 10511 Z3 L17 Q5 10512 Z3 L17 Q6 10513 Z3 L17 Q7 10514 Z3 L17 Q8 10515 Z3 L17 Q9 10516 Z3 L17 Q10 10517 Z3 L17 Q11 10518 Z3 L17 Q12 10519 Z3 L17 Q13 10520 Z3 L17 Q14 10521 Z3 L17 Q15 10522 Z3 L17 Q16 10523 Z3 L17 Q17 10524 Z3 L17 Q18 10525 Z3 L17 Q19 10526 Z3 L17 Q20 10527 Z3 L17 Q21 10528 Z3 L17 Q22 10529 Z3 L17 Q23 10530 Z3 L17 Q24 10531 Z3 L17 Q25 10532 Z3 L17 Q26 10533 Z3 L17 Q27 10534 Z3 L17 Q28 10535 Z3 L17 Q29 10536 Z3 L17 Q30 10537 Z3 L17 Q31 10538 Z3 L17 Q32 10539 Z3 L17 Q33 10540 Z3 L17 Q34 10541 Z3 L17 Q35 10542 Z3 L17 Q36 10543 Z3 L17 Q37 10544 Z3 L17 Q38 10545 Z3 L17 Q39 10546 Z3 L17 Q40 10547 Z3 L17 Q41 10548 Z3 L17 Q42 10549 Z3 L17 Q43 10550 Z3 L17 Q44 10551 Z3 L17 Q45 10552 Z3 L17 Q46 10553 Z3 L17 Q47 10554 Z3 L17 Q48 10555 Z3 L17 Q49 10556 Z3 L17 Q50 10557 Z3 L17 Q51 10558 Z3 L17 Q52 10559 Z3 L17 Q53 10560 Z3 L17 Q54 10561 Z3 L17 Q55 10562 Z3 L17 Q56 10563 Z3 L17 Q57 10564 Z3 L17 Q58 10565 Z3 L17 Q59 10566 Z3 L17 Q60 10567 Z3 L17 Q61 10568 Z3 L17 Q62 10569 Z3 L17 Q63 10570 Z3 L17 Q64 10571 Z3 L17 Q65 10572 Z3 L17 Q66 10573 Z3 L17 Q67 10574 Z3 L17 Q68 10575 Z3 L17 Q69 10576 Z3 L17 Q70 10577 Z3 L17 Q71 10578 Z3 L17 Q72 10579 Z3 L17 Q73 10580 Z3 L17 Q74 10581 Z3 L17 Q75 10582 Z3 L17 Q76 10583 Z3 L17 Q77 10584 Z3 L17 Q78 10585 Z3 L17 Q79 10586 Z3 L17 Q80 10587 Z3 L17 Q81 10588 Z3 L17 Q82 10589 Z3 L17 Q83 10590 Z3 L17 Q84 10591 Z3 L17 Q85 10592 Z3 L17 Q86 10593 Z3 L17 Q87 10594 Z3 L17 Q88 10595 Z3 L17 Q89 10596 Z3 L17 Q90 10597 Z3 L17 Q91 10598 Z3 L17 Q92 10599 Z3 L17 Q93 10600 Z3 L17 Q94 10601 Z3 L17 Q95 10602 Z3 L17 Q96 10603 Z3 L17 Q97 10604 Z3 L17 Q98 10605 Z3 L17 Q99 10606 Z3 L17 Q100 10607 Z3 L17 Q101 10608 Z3 L17 Q102 10609 Z3 L17 Q103 10610 Z3 L18 Q1 10611 Z3 L18 Q2 10612 Z3 L18 Q3 10613 Z3 L18 Q4 10614 Z3 L18 Q5 10615 Z3 L18 Q6 10616 Z3 L18 Q7 10617 Z3 L18 Q8 10618 Z3 L18 Q9 10619 Z3 L18 Q10 10620 Z3 L18 Q11 10621 Z3 L18 Q12 10622 Z3 L18 Q13 10623 Z3 L18 Q14 10624 Z3 L18 Q15 10625 Z3 L18 Q16

TABLE 1-59 10626 Z3 L18 Q17 10627 Z3 L18 Q18 10628 Z3 L18 Q19 10629 Z3 L18 Q20 10630 Z3 L18 Q21 10631 Z3 L18 Q22 10632 Z3 L18 Q23 10633 Z3 L18 Q24 10634 Z3 L18 Q25 10635 Z3 L18 Q26 10636 Z3 L18 Q27 10637 Z3 L18 Q28 10638 Z3 L18 Q29 10639 Z3 L18 Q30 10640 Z3 L18 Q31 10641 Z3 L18 Q32 10642 Z3 L18 Q33 10643 Z3 L18 Q34 10644 Z3 L18 Q35 10645 Z3 L18 Q36 10646 Z3 L18 Q37 10647 Z3 L18 Q38 10648 Z3 L18 Q39 10649 Z3 L18 Q40 10650 Z3 L18 Q41 10651 Z3 L18 Q42 10652 Z3 L18 Q43 10653 Z3 L18 Q44 10654 Z3 L18 Q45 10655 Z3 L18 Q46 10656 Z3 L18 Q47 10657 Z3 L18 Q48 10658 Z3 L18 Q49 10659 Z3 L18 Q50 10660 Z3 L18 Q51 10661 Z3 L18 Q52 10662 Z3 L18 Q53 10663 Z3 L18 Q54 10664 Z3 L18 Q55 10665 Z3 L18 Q56 10666 Z3 L18 Q57 10667 Z3 L18 Q58 10668 Z3 L18 Q59 10669 Z3 L18 Q60 10670 Z3 L18 Q61 10671 Z3 L18 Q62 10672 Z3 L18 Q63 10673 Z3 L18 Q64 10674 Z3 L18 Q65 10675 Z3 L18 Q66 10676 Z3 L18 Q67 10677 Z3 L18 Q68 10678 Z3 L18 Q69 10679 Z3 L18 Q70 10680 Z3 L18 Q71 10681 Z3 L18 Q72 10682 Z3 L18 Q73 10683 Z3 L18 Q74 10684 Z3 L18 Q75 10685 Z3 L18 Q76 10686 Z3 L18 Q77 10687 Z3 L18 Q78 10688 Z3 L18 Q79 10689 Z3 L18 Q80 10690 Z3 L18 Q81 10691 Z3 L18 Q82 10692 Z3 L18 Q83 10693 Z3 L18 Q84 10694 Z3 L18 Q85 10695 Z3 L18 Q86 10696 Z3 L18 Q87 10697 Z3 L18 Q88 10698 Z3 L18 Q89 10699 Z3 L18 Q90 10700 Z3 L18 Q91 10701 Z3 L18 Q92 10702 Z3 L18 Q93 10703 Z3 L18 Q94 10704 Z3 L18 Q95 10705 Z3 L18 Q96 10706 Z3 L18 Q97 10707 Z3 L18 Q98 10708 Z3 L18 Q99 10709 Z3 L18 Q100 10710 Z3 L18 Q101 10711 Z3 L18 Q102 10712 Z3 L18 Q103 10713 Z3 L19 Q1 10714 Z3 L19 Q2 10715 Z3 L19 Q3 10716 Z3 L19 Q4 10717 Z3 L19 Q5 10718 Z3 L19 Q6 10719 Z3 L19 Q7 10720 Z3 L19 Q8 10721 Z3 L19 Q9 10722 Z3 L19 Q10 10723 Z3 L19 Q11 10724 Z3 L19 Q12 10725 Z3 L19 Q13 10726 Z3 L19 Q14 10727 Z3 L19 Q15 10728 Z3 L19 Q16 10729 Z3 L19 Q17 10730 Z3 L19 Q18 10731 Z3 L19 Q19 10732 Z3 L19 Q20 10733 Z3 L19 Q21 10734 Z3 L19 Q22 10735 Z3 L19 Q23 10736 Z3 L19 Q24 10737 Z3 L19 Q25 10738 Z3 L19 Q26 10739 Z3 L19 Q27 10740 Z3 L19 Q28 10741 Z3 L19 Q29 10742 Z3 L19 Q30 10743 Z3 L19 Q31 10744 Z3 L19 Q32 10745 Z3 L19 Q33 10746 Z3 L19 Q34 10747 Z3 L19 Q35 10748 Z3 L19 Q36 10749 Z3 L19 Q37 10750 Z3 L19 Q38 10751 Z3 L19 Q39 10752 Z3 L19 Q40 10753 Z3 L19 Q41 10754 Z3 L19 Q42 10755 Z3 L19 Q43 10756 Z3 L19 Q44 10757 Z3 L19 Q45 10758 Z3 L19 Q46 10759 Z3 L19 Q47 10760 Z3 L19 Q48 10761 Z3 L19 Q49 10762 Z3 L19 Q50 10763 Z3 L19 Q51 10764 Z3 L19 Q52 10765 Z3 L19 Q53 10766 Z3 L19 Q54 10767 Z3 L19 Q55 10768 Z3 L19 Q56 10769 Z3 L19 Q57 10770 Z3 L19 Q58 10771 Z3 L19 Q59 10772 Z3 L19 Q60 10773 Z3 L19 Q61 10774 Z3 L19 Q62 10775 Z3 L19 Q63 10776 Z3 L19 Q64 10777 Z3 L19 Q65 10778 Z3 L19 Q66 10779 Z3 L19 Q67 10780 Z3 L19 Q68 10781 Z3 L19 Q69 10782 Z3 L19 Q70 10783 Z3 L19 Q71 10784 Z3 L19 Q72 10785 Z3 L19 Q73 10786 Z3 L19 Q74 10787 Z3 L19 Q75 10788 Z3 L19 Q76 10789 Z3 L19 Q77 10790 Z3 L19 Q78 10791 Z3 L19 Q79 10792 Z3 L19 Q80 10793 Z3 L19 Q81 10794 Z3 L19 Q82 10795 Z3 L19 Q83 10796 Z3 L19 Q84 10797 Z3 L19 Q85 10798 Z3 L19 Q86 10799 Z3 L19 Q87 10800 Z3 L19 Q88 10801 Z3 L19 Q89 10802 Z3 L19 Q90 10803 Z3 L19 Q91 10804 Z3 L19 Q92 10805 Z3 L19 Q93 10806 Z3 L19 Q94 10807 Z3 L19 Q95 10808 Z3 L19 Q96 10809 Z3 L19 Q97 10810 Z3 L19 Q98 10811 Z3 L19 Q99 10812 Z3 L19 Q100 10813 Z3 L19 Q101 10814 Z3 L19 Q102 10815 Z3 L19 Q103 10816 Z3 L20 Q1 10817 Z3 L20 Q2 10818 Z3 L20 Q3 10819 Z3 L20 Q4 10820 Z3 L20 Q5 10821 Z3 L20 Q6 10822 Z3 L20 Q7 10823 Z3 L20 Q8 10824 Z3 L20 Q9 10825 Z3 L20 Q10 10826 Z3 L20 Q11

TABLE 1-60 10827 Z3 L20 Q12 10828 Z3 L20 Q13 10829 Z3 L20 Q14 10830 Z3 L20 Q15 10831 Z3 L20 Q16 10832 Z3 L20 Q17 10833 Z3 L20 Q18 10834 Z3 L20 Q19 10835 Z3 L20 Q20 10836 Z3 L20 Q21 10837 Z3 L20 Q22 10838 Z3 L20 Q23 10839 Z3 L20 Q24 10840 Z3 L20 Q25 10841 Z3 L20 Q26 10842 Z3 L20 Q27 10843 Z3 L20 Q28 10844 Z3 L20 Q29 10845 Z3 L20 Q30 10846 Z3 L20 Q31 10847 Z3 L20 Q32 10848 Z3 L20 Q33 10849 Z3 L20 Q34 10850 Z3 L20 Q35 10851 Z3 L20 Q36 10852 Z3 L20 Q37 10853 Z3 L20 Q38 10854 Z3 L20 Q39 10855 Z3 L20 Q40 10856 Z3 L20 Q41 10857 Z3 L20 Q42 10858 Z3 L20 Q43 10859 Z3 L20 Q44 10860 Z3 L20 Q45 10861 Z3 L20 Q46 10862 Z3 L20 Q47 10863 Z3 L20 Q48 10864 Z3 L20 Q49 10865 Z3 L20 Q50 10866 Z3 L20 Q51 10867 Z3 L20 Q52 10868 Z3 L20 Q53 10869 Z3 L20 Q54 10870 Z3 L20 Q55 10871 Z3 L20 Q56 10872 Z3 L20 Q57 10873 Z3 L20 Q58 10874 Z3 L20 Q59 10875 Z3 L20 Q60 10876 Z3 L20 Q61 10877 Z3 L20 Q62 10878 Z3 L20 Q63 10879 Z3 L20 Q64 10880 Z3 L20 Q65 10881 Z3 L20 Q66 10882 Z3 L20 Q67 10883 Z3 L20 Q68 10884 Z3 L20 Q69 10885 Z3 L20 Q70 10886 Z3 L20 Q71 10887 Z3 L20 Q72 10888 Z3 L20 Q73 10889 Z3 L20 Q74 10890 Z3 L20 Q75 10891 Z3 L20 Q76 10892 Z3 L20 Q77 10893 Z3 L20 Q78 10894 Z3 L20 Q79 10895 Z3 L20 Q80 10896 Z3 L20 Q81 10897 Z3 L20 Q82 10898 Z3 L20 Q83 10899 Z3 L20 Q84 10900 Z3 L20 Q85 10901 Z3 L20 Q86 10902 Z3 L20 Q87 10903 Z3 L20 Q88 10904 Z3 L20 Q89 10905 Z3 L20 Q90 10906 Z3 L20 Q91 10907 Z3 L20 Q92 10908 Z3 L20 Q93 10909 Z3 L20 Q94 10910 Z3 L20 Q95 10911 Z3 L20 Q96 10912 Z3 L20 Q97 10913 Z3 L20 Q98 10914 Z3 L20 Q99 10915 Z3 L20 Q100 10916 Z3 L20 Q101 10917 Z3 L20 Q102 10918 Z3 L20 Q103 10919 Z3 L21 Q1 10920 Z3 L21 Q2 10921 Z3 L21 Q3 10922 Z3 L21 Q4 10923 Z3 L21 Q5 10924 Z3 L21 Q6 10925 Z3 L21 Q7 10926 Z3 L21 Q8 10927 Z3 L21 Q9 10928 Z3 L21 Q10 10929 Z3 L21 Q11 10930 Z3 L21 Q12 10931 Z3 L21 Q13 10932 Z3 L21 Q14 10933 Z3 L21 Q15 10934 Z3 L21 Q16 10935 Z3 L21 Q17 10936 Z3 L21 Q18 10937 Z3 L21 Q19 10938 Z3 L21 Q20 10939 Z3 L21 Q21 10940 Z3 L21 Q22 10941 Z3 L21 Q23 10942 Z3 L21 Q24 10943 Z3 L21 Q25 10944 Z3 L21 Q26 10945 Z3 L21 Q27 10946 Z3 L21 Q28 10947 Z3 L21 Q29 10948 Z3 L21 Q30 10949 Z3 L21 Q31 10950 Z3 L21 Q32 10951 Z3 L21 Q33 10952 Z3 L21 Q34 10953 Z3 L21 Q35 10954 Z3 L21 Q36 10955 Z3 L21 Q37 10956 Z3 L21 Q38 10957 Z3 L21 Q39 10958 Z3 L21 Q40 10959 Z3 L21 Q41 10960 Z3 L21 Q42 10961 Z3 L21 Q43 10962 Z3 L21 Q44 10963 Z3 L21 Q45 10964 Z3 L21 Q46 10965 Z3 L21 Q47 10966 Z3 L21 Q48 10967 Z3 L21 Q49 10968 Z3 L21 Q50 10969 Z3 L21 Q51 10970 Z3 L21 Q52 10971 Z3 L21 Q53 10972 Z3 L21 Q54 10973 Z3 L21 Q55 10974 Z3 L21 Q56 10975 Z3 L21 Q57 10976 Z3 L21 Q58 10977 Z3 L21 Q59 10978 Z3 L21 Q60 10979 Z3 L21 Q61 10980 Z3 L21 Q62 10981 Z3 L21 Q63 10982 Z3 L21 Q64 10983 Z3 L21 Q65 10984 Z3 L21 Q66 10985 Z3 L21 Q67 10986 Z3 L21 Q68 10987 Z3 L21 Q69 10988 Z3 L21 Q70 10989 Z3 L21 Q71 10990 Z3 L21 Q72 10991 Z3 L21 Q73 10992 Z3 L21 Q74 10993 Z3 L21 Q75 10994 Z3 L21 Q76 10995 Z3 L21 Q77 10996 Z3 L21 Q78 10997 Z3 L21 Q79 10998 Z3 L21 Q80 10999 Z3 L21 Q81 11000 Z3 L21 Q82 11001 Z3 L21 Q83 11002 Z3 L21 Q84 11003 Z3 L21 Q85 11004 Z3 L21 Q86 11005 Z3 L21 Q87 11006 Z3 L21 Q88 11007 Z3 L21 Q89 11008 Z3 L21 Q90 11009 Z3 L21 Q91 11010 Z3 L21 Q92 11011 Z3 L21 Q93 11012 Z3 L21 Q94 11013 Z3 L21 Q95 11014 Z3 L21 Q96 11015 Z3 L21 Q97 11016 Z3 L21 Q98 11017 Z3 L21 Q99 11018 Z3 L21 Q100 11019 Z3 L21 Q101 11020 Z3 L21 Q102 11021 Z3 L21 Q103 11022 Z3 L22 Q1 11023 Z3 L22 Q2 11024 Z3 L22 Q3 11025 Z3 L22 Q4 11026 Z3 L22 Q5 11027 Z3 L22 Q6

TABLE 1-61 11028 Z3 L22 Q7 11029 Z3 L22 Q8 11030 Z3 L22 Q9 11031 Z3 L22 Q10 11032 Z3 L22 Q11 11033 Z3 L22 Q12 11034 Z3 L22 Q13 11035 Z3 L22 Q14 11036 Z3 L22 Q15 11037 Z3 L22 Q16 11038 Z3 L22 Q17 11039 Z3 L22 Q18 11040 Z3 L22 Q19 11041 Z3 L22 Q20 11042 Z3 L22 Q21 11043 Z3 L22 Q22 11044 Z3 L22 Q23 11045 Z3 L22 Q24 11046 Z3 L22 Q25 11047 Z3 L22 Q26 11048 Z3 L22 Q27 11049 Z3 L22 Q28 11050 Z3 L22 Q29 11051 Z3 L22 Q30 11052 Z3 L22 Q31 11053 Z3 L22 Q32 11054 Z3 L22 Q33 11055 Z3 L22 Q34 11056 Z3 L22 Q35 11057 Z3 L22 Q36 11058 Z3 L22 Q37 11059 Z3 L22 Q38 11060 Z3 L22 Q39 11061 Z3 L22 Q40 11062 Z3 L22 Q41 11063 Z3 L22 Q42 11064 Z3 L22 Q43 11065 Z3 L22 Q44 11066 Z3 L22 Q45 11067 Z3 L22 Q46 11068 Z3 L22 Q47 11069 Z3 L22 Q48 11070 Z3 L22 Q49 11071 Z3 L22 Q50 11072 Z3 L22 Q51 11073 Z3 L22 Q52 11074 Z3 L22 Q53 11075 Z3 L22 Q54 11076 Z3 L22 Q55 11077 Z3 L22 Q56 11078 Z3 L22 Q57 11079 Z3 L22 Q58 11080 Z3 L22 Q59 11081 Z3 L22 Q60 11082 Z3 L22 Q61 11083 Z3 L22 Q62 11084 Z3 L22 Q63 11085 Z3 L22 Q64 11086 Z3 L22 Q65 11087 Z3 L22 Q66 11088 Z3 L22 Q67 11089 Z3 L22 Q68 11090 Z3 L22 Q69 11091 Z3 L22 Q70 11092 Z3 L22 Q71 11093 Z3 L22 Q72 11094 Z3 L22 Q73 11095 Z3 L22 Q74 11096 Z3 L22 Q75 11097 Z3 L22 Q76 11098 Z3 L22 Q77 11099 Z3 L22 Q78 11100 Z3 L22 Q79 11101 Z3 L22 Q80 11102 Z3 L22 Q81 11103 Z3 L22 Q82 11104 Z3 L22 Q83 11105 Z3 L22 Q84 11106 Z3 L22 Q85 11107 Z3 L22 Q86 11108 Z3 L22 Q87 11109 Z3 L22 Q88 11110 Z3 L22 Q89 11111 Z3 L22 Q90 11112 Z3 L22 Q91 11113 Z3 L22 Q92 11114 Z3 L22 Q93 11115 Z3 L22 Q94 11116 Z3 L22 Q95 11117 Z3 L22 Q96 11118 Z3 L22 Q97 11119 Z3 L22 Q98 11120 Z3 L22 Q99 11121 Z3 L22 Q100 11122 Z3 L22 Q101 11123 Z3 L22 Q102 11124 Z3 L22 Q103 11125 Z3 L23 Q1 11126 Z3 L23 Q2 11127 Z3 L23 Q3 11128 Z3 L23 Q4 11129 Z3 L23 Q5 11130 Z3 L23 Q6 11131 Z3 L23 Q7 11132 Z3 L23 Q8 11133 Z3 L23 Q9 11134 Z3 L23 Q10 11135 Z3 L23 Q11 11136 Z3 L23 Q12 11137 Z3 L23 Q13 11138 Z3 L23 Q14 11139 Z3 L23 Q15 11140 Z3 L23 Q16 11141 Z3 L23 Q17 11142 Z3 L23 Q18 11143 Z3 L23 Q19 11144 Z3 L23 Q20 11145 Z3 L23 Q21 11146 Z3 L23 Q22 11147 Z3 L23 Q23 11148 Z3 L23 Q24 11149 Z3 L23 Q25 11150 Z3 L23 Q26 11151 Z3 L23 Q27 11152 Z3 L23 Q28 11153 Z3 L23 Q29 11154 Z3 L23 Q30 11155 Z3 L23 Q31 11156 Z3 L23 Q32 11157 Z3 L23 Q33 11158 Z3 L23 Q34 11159 Z3 L23 Q35 11160 Z3 L23 Q36 11161 Z3 L23 Q37 11162 Z3 L23 Q38 11163 Z3 L23 Q39 11164 Z3 L23 Q40 11165 Z3 L23 Q41 11166 Z3 L23 Q42 11167 Z3 L23 Q43 11168 Z3 L23 Q44 11169 Z3 L23 Q45 11170 Z3 L23 Q46 11171 Z3 L23 Q47 11172 Z3 L23 Q48 11173 Z3 L23 Q49 11174 Z3 L23 Q50 11175 Z3 L23 Q51 11176 Z3 L23 Q52 11177 Z3 L23 Q53 11178 Z3 L23 Q54 11179 Z3 L23 Q55 11180 Z3 L23 Q56 11181 Z3 L23 Q57 11182 Z3 L23 Q58 11183 Z3 L23 Q59 11184 Z3 L23 Q60 11185 Z3 L23 Q61 11186 Z3 L23 Q62 11187 Z3 L23 Q63 11188 Z3 L23 Q64 11189 Z3 L23 Q65 11190 Z3 L23 Q66 11191 Z3 L23 Q67 11192 Z3 L23 Q68 11193 Z3 L23 Q69 11194 Z3 L23 Q70 11195 Z3 L23 Q71 11196 Z3 L23 Q72 11197 Z3 L23 Q73 11198 Z3 L23 Q74 11199 Z3 L23 Q75 11200 Z3 L23 Q76 11201 Z3 L23 Q77 11202 Z3 L23 Q78 11203 Z3 L23 Q79 11204 Z3 L23 Q80 11205 Z3 L23 Q81 11206 Z3 L23 Q82 11207 Z3 L23 Q83 11208 Z3 L23 Q84 11209 Z3 L23 Q85 11210 Z3 L23 Q86 11211 Z3 L23 Q87 11212 Z3 L23 Q88 11213 Z3 L23 Q89 11214 Z3 L23 Q90 11215 Z3 L23 Q91 11216 Z3 L23 Q92 11217 Z3 L23 Q93 11218 Z3 L23 Q94 11219 Z3 L23 Q95 11220 Z3 L23 Q96 11221 Z3 L23 Q97 11222 Z3 L23 Q98 11223 Z3 L23 Q99 11224 Z3 L23 Q100 11225 Z3 L23 Q101 11226 Z3 L23 Q102 11227 Z3 L23 Q103 11228 Z3 L24 Q1

TABLE 1-62 11229 Z3 L24 Q2 11230 Z3 L24 Q3 11231 Z3 L24 Q4 11232 Z3 L24 Q5 11233 Z3 L24 Q6 11234 Z3 L24 Q7 11235 Z3 L24 Q8 11236 Z3 L24 Q9 11237 Z3 L24 Q10 11238 Z3 L24 Q11 11239 Z3 L24 Q12 11240 Z3 L24 Q13 11241 Z3 L24 Q14 11242 Z3 L24 Q15 11243 Z3 L24 Q16 11244 Z3 L24 Q17 11245 Z3 L24 Q18 11246 Z3 L24 Q19 11247 Z3 L24 Q20 11248 Z3 L24 Q21 11249 Z3 L24 Q22 11250 Z3 L24 Q23 11251 Z3 L24 Q24 11252 Z3 L24 Q25 11253 Z3 L24 Q26 11254 Z3 L24 Q27 11255 Z3 L24 Q28 11256 Z3 L24 Q29 11257 Z3 L24 Q30 11258 Z3 L24 Q31 11259 Z3 L24 Q32 11260 Z3 L24 Q33 11261 Z3 L24 Q34 11262 Z3 L24 Q35 11263 Z3 L24 Q36 11264 Z3 L24 Q37 11265 Z3 L24 Q38 11266 Z3 L24 Q39 11267 Z3 L24 Q40 11268 Z3 L24 Q41 11269 Z3 L24 Q42 11270 Z3 L24 Q43 11271 Z3 L24 Q44 11272 Z3 L24 Q45 11273 Z3 L24 Q46 11274 Z3 L24 Q47 11275 Z3 L24 Q48 11276 Z3 L24 Q49 11277 Z3 L24 Q50 11278 Z3 L24 Q51 11279 Z3 L24 Q52 11280 Z3 L24 Q53 11281 Z3 L24 Q54 11282 Z3 L24 Q55 11283 Z3 L24 Q56 11284 Z3 L24 Q57 11285 Z3 L24 Q58 11286 Z3 L24 Q59 11287 Z3 L24 Q60 11288 Z3 L24 Q61 11289 Z3 L24 Q62 11290 Z3 L24 Q63 11291 Z3 L24 Q64 11292 Z3 L24 Q65 11293 Z3 L24 Q66 11294 Z3 L24 Q67 11295 Z3 L24 Q68 11296 Z3 L24 Q69 11297 Z3 L24 Q70 11298 Z3 L24 Q71 11299 Z3 L24 Q72 11300 Z3 L24 Q73 11301 Z3 L24 Q74 11302 Z3 L24 Q75 11303 Z3 L24 Q76 11304 Z3 L24 Q77 11305 Z3 L24 Q78 11306 Z3 L24 Q79 11307 Z3 L24 Q80 11308 Z3 L24 Q81 11309 Z3 L24 Q82 11310 Z3 L24 Q83 11311 Z3 L24 Q84 11312 Z3 L24 Q85 11313 Z3 L24 Q86 11314 Z3 L24 Q87 11315 Z3 L24 Q88 11316 Z3 L24 Q89 11317 Z3 L24 Q90 11318 Z3 L24 Q91 11319 Z3 L24 Q92 11320 Z3 L24 Q93 11321 Z3 L24 Q94 11322 Z3 L24 Q95 11323 Z3 L24 Q96 11324 Z3 L24 Q97 11325 Z3 L24 Q98 11326 Z3 L24 Q99 11327 Z3 L24 Q100 11328 Z3 L24 Q101 11329 Z3 L24 Q102 11330 Z3 L24 Q103 11331 Z3 L25 Q1 11332 Z3 L25 Q2 11333 Z3 L25 Q3 11334 Z3 L25 Q4 11335 Z3 L25 Q5 11336 Z3 L25 Q6 11337 Z3 L25 Q7 11338 Z3 L25 Q8 11339 Z3 L25 Q9 11340 Z3 L25 Q10 11341 Z3 L25 Q11 11342 Z3 L25 Q12 11343 Z3 L25 Q13 11344 Z3 L25 Q14 11345 Z3 L25 Q15 11346 Z3 L25 Q16 11347 Z3 L25 Q17 11348 Z3 L25 Q18 11349 Z3 L25 Q19 11350 Z3 L25 Q20 11351 Z3 L25 Q21 11352 Z3 L25 Q22 11353 Z3 L25 Q23 11354 Z3 L25 Q24 11355 Z3 L25 Q25 11356 Z3 L25 Q26 11357 Z3 L25 Q27 11358 Z3 L25 Q28 11359 Z3 L25 Q29 11360 Z3 L25 Q30 11361 Z3 L25 Q31 11362 Z3 L25 Q32 11363 Z3 L25 Q33 11364 Z3 L25 Q34 11365 Z3 L25 Q35 11366 Z3 L25 Q36 11367 Z3 L25 Q37 11368 Z3 L25 Q38 11369 Z3 L25 Q39 11370 Z3 L25 Q40 11371 Z3 L25 Q41 11372 Z3 L25 Q42 11373 Z3 L25 Q43 11374 Z3 L25 Q44 11375 Z3 L25 Q45 11376 Z3 L25 Q46 11377 Z3 L25 Q47 11378 Z3 L25 Q48 11379 Z3 L25 Q49 11380 Z3 L25 Q50 11381 Z3 L25 Q51 11332 Z3 L25 Q52 11383 Z3 L25 Q53 11384 Z3 L25 Q54 11385 Z3 L25 Q55 11386 Z3 L25 Q56 11387 Z3 L25 Q57 11388 Z3 L25 Q58 11389 Z3 L25 Q59 11390 Z3 L25 Q60 11391 Z3 L25 Q61 11392 Z3 L25 Q62 11393 Z3 L25 Q63 11394 Z3 L25 Q64 11395 Z3 L25 Q65 11396 Z3 L25 Q66 11397 Z3 L25 Q67 11398 Z3 L25 Q68 11399 Z3 L25 Q69 11400 Z3 L25 Q70 11401 Z3 L25 Q71 11402 Z3 L25 Q72 11403 Z3 L25 Q73 11404 Z3 L25 Q74 11405 Z3 L25 Q75 11406 Z3 L25 Q76 11407 Z3 L25 Q77 11408 Z3 L25 Q78 11409 Z3 L25 Q79 11410 Z3 L25 Q80 11411 Z3 L25 Q81 11412 Z3 L25 Q82 11413 Z3 L25 Q83 11414 Z3 L25 Q84 11415 Z3 L25 Q85 11416 Z3 L25 Q86 11417 Z3 L25 Q87 11418 Z3 L25 Q88 11419 Z3 L25 Q89 11420 Z3 L25 Q90 11421 Z3 L25 Q91 11422 Z3 L25 Q92 11423 Z3 L25 Q93 11424 Z3 L25 Q94 11425 Z3 L25 Q95 11426 Z3 L25 Q96 11427 Z3 L25 Q97 11428 Z3 L25 Q98 11429 Z3 L25 Q99

TABLE 1-63 11430 Z3 L25 Q100 11431 Z3 L25 Q101 11432 Z3 L25 Q102 11433 Z3 L25 Q103 11434 Z3 L26 Q1 11435 Z3 L26 Q2 11436 Z3 L26 Q3 11437 Z3 L26 Q4 11438 Z3 L26 Q5 11439 Z3 L26 Q6 11440 Z3 L26 Q7 11441 Z3 L26 Q8 11442 Z3 L26 Q9 11443 Z3 L26 Q10 11444 Z3 L26 Q11 11445 Z3 L26 Q12 11446 Z3 L26 Q13 11447 Z3 L26 Q14 11448 Z3 L26 Q15 11449 Z3 L26 Q16 11450 Z3 L26 Q17 11451 Z3 L26 Q18 11452 Z3 L26 Q19 11453 Z3 L26 Q20 11454 Z3 L26 Q21 11455 Z3 L26 Q22 11456 Z3 L26 Q23 11457 Z3 L26 Q24 11458 Z3 L26 Q25 11459 Z3 L26 Q26 11460 Z3 L26 Q27 11461 Z3 L26 Q28 11462 Z3 L26 Q29 11463 Z3 L26 Q30 11464 Z3 L26 Q31 11465 Z3 L26 Q32 11466 Z3 L26 Q33 11467 Z3 L26 Q34 11468 Z3 L26 Q35 11469 Z3 L26 Q36 11470 Z3 L26 Q37 11471 Z3 L26 Q38 11472 Z3 L26 Q39 11473 Z3 L26 Q40 11474 Z3 L26 Q41 11475 Z3 L26 Q42 11476 Z3 L26 Q43 11477 Z3 L26 Q44 11478 Z3 L26 Q45 11479 Z3 L26 Q46 11480 Z3 L26 Q47 11481 Z3 L26 Q48 11482 Z3 L26 Q49 11483 Z3 L26 Q50 11484 Z3 L26 Q51 11485 Z3 L26 Q52 11486 Z3 L26 Q53 11487 Z3 L26 Q54 11488 Z3 L26 Q55 11489 Z3 L26 Q56 11490 Z3 L26 Q57 11491 Z3 L26 Q58 11492 Z3 L26 Q59 11493 Z3 L26 Q60 11494 Z3 L26 Q61 11495 Z3 L26 Q62 11496 Z3 L26 Q63 11497 Z3 L26 Q64 11498 Z3 L26 Q65 11499 Z3 L26 Q66 11500 Z3 L26 Q67 11501 Z3 L26 Q68 11502 Z3 L26 Q69 11503 Z3 L26 Q70 11504 Z3 L26 Q71 11505 Z3 L26 Q72 11506 Z3 L26 Q73 11507 Z3 L26 Q74 11508 Z3 L26 Q75 11509 Z3 L26 Q76 11510 Z3 L26 Q77 11511 Z3 L26 Q78 11512 Z3 L26 Q79 11513 Z3 L26 Q80 11514 Z3 L26 Q81 11515 Z3 L26 Q82 11516 Z3 L26 Q83 11517 Z3 L26 Q84 11518 Z3 L26 Q85 11519 Z3 L26 Q86 11520 Z3 L26 Q87 11521 Z3 L26 Q88 11522 Z3 L26 Q89 11523 Z3 L26 Q90 11524 Z3 L26 Q91 11525 Z3 L26 Q92 11526 Z3 L26 Q93 11527 Z3 L26 Q94 11528 Z3 L26 Q95 11529 Z3 L26 Q96 11530 Z3 L26 Q97 11531 Z3 L26 Q98 11532 Z3 L26 Q99 11533 Z3 L26 Q100 11534 Z3 L26 Q101 11535 Z3 L26 Q102 11536 Z3 L26 Q103 11537 Z3 L27 Q1 11538 Z3 L27 Q2 11539 Z3 L27 Q3 11540 Z3 L27 Q4 11541 Z3 L27 Q5 11542 Z3 L27 Q6 11543 Z3 L27 Q7 11544 Z3 L27 Q8 11545 Z3 L27 Q9 11546 Z3 L27 Q10 11547 Z3 L27 Q11 11548 Z3 L27 Q12 11549 Z3 L27 Q13 11550 Z3 L27 Q14 11551 Z3 L27 Q15 11552 Z3 L27 Q16 11553 Z3 L27 Q17 11554 Z3 L27 Q18 11555 Z3 L27 Q19 11556 Z3 L27 Q20 11557 Z3 L27 Q21 11558 Z3 L27 Q22 11559 Z3 L27 Q23 11560 Z3 L27 Q24 11561 Z3 L27 Q25 11562 Z3 L27 Q26 11563 Z3 L27 Q27 11564 Z3 L27 Q28 11565 Z3 L27 Q29 11566 Z3 L27 Q30 11567 Z3 L27 Q31 11568 Z3 L27 Q32 11569 Z3 L27 Q33 11570 Z3 L27 Q34 11571 Z3 L27 Q35 11572 Z3 L27 Q36 11573 Z3 L27 Q37 11574 Z3 L27 Q38 11575 Z3 L27 Q39 11576 Z3 L27 Q40 11577 Z3 L27 Q41 11578 Z3 L27 Q42 11579 Z3 L27 Q43 11580 Z3 L27 Q44 11581 Z3 L27 Q45 11582 Z3 L27 Q46 11583 Z3 L27 Q47 11584 Z3 L27 Q48 11585 Z3 L27 Q49 11586 Z3 L27 Q50 11587 Z3 L27 Q51 11588 Z3 L27 Q52 11589 Z3 L27 Q53 11590 Z3 L27 Q54 11591 Z3 L27 Q55 11592 Z3 L27 Q56 11593 Z3 L27 Q57 11594 Z3 L27 Q58 11595 Z3 L27 Q59 11596 Z3 L27 Q60 11597 Z3 L27 Q61 11598 Z3 L27 Q62 11599 Z3 L27 Q63 11600 Z3 L27 Q64 11601 Z3 L27 Q65 11602 Z3 L27 Q66 11603 Z3 L27 Q67 11604 Z3 L27 Q68 11605 Z3 L27 Q69 11606 Z3 L27 Q70 11607 Z3 L27 Q71 11608 Z3 L27 Q72 11609 Z3 L27 Q73 11610 Z3 L27 Q74 11611 Z3 L27 Q75 11612 Z3 L27 Q76 11613 Z3 L27 Q77 11614 Z3 L27 Q78 11615 Z3 L27 Q79 11616 Z3 L27 Q80 11617 Z3 L27 Q81 11618 Z3 L27 Q82 11619 Z3 L27 Q83 11620 Z3 L27 Q84 11621 Z3 L27 Q85 11622 Z3 L27 Q86 11623 Z3 L27 Q87 11624 Z3 L27 Q88 11625 Z3 L27 Q89 11626 Z3 L27 Q90 11627 Z3 L27 Q91 11628 Z3 L27 Q92 11629 Z3 L27 Q93 11630 Z3 L27 Q94

TABLE 1-64 11631 Z3 L27 Q95 11632 Z3 L27 Q96 11633 Z3 L27 Q97 11634 Z3 L27 Q98 11635 Z3 L27 Q99 11636 Z3 L27 Q100 11637 Z3 L27 Q101 11638 Z3 L27 Q102 11639 Z3 L27 Q103 11640 Z3 L28 Q1 11641 Z3 L28 Q2 11642 Z3 L28 Q3 11643 Z3 L28 Q4 11644 Z3 L28 Q5 11645 Z3 L28 Q6 11646 Z3 L28 Q7 11647 Z3 L28 Q8 11648 Z3 L28 Q9 11649 Z3 L28 Q10 11650 Z3 L28 Q11 11651 Z3 L28 Q12 11652 Z3 L28 Q13 11653 Z3 L28 Q14 11654 Z3 L28 Q15 11655 Z3 L28 Q16 11656 Z3 L28 Q17 11657 Z3 L28 Q18 11658 Z3 L28 Q19 11659 Z3 L28 Q20 11660 Z3 L28 Q21 11661 Z3 L28 Q22 11662 Z3 L28 Q23 11663 Z3 L28 Q24 11664 Z3 L28 Q25 11665 Z3 L28 Q26 11666 Z3 L28 Q27 11667 Z3 L28 Q28 11668 Z3 L28 Q29 11669 Z3 L28 Q30 11670 Z3 L28 Q31 11671 Z3 L28 Q32 11672 Z3 L28 Q33 11673 Z3 L28 Q34 11674 Z3 L28 Q35 11675 Z3 L28 Q36 11676 Z3 L28 Q37 11677 Z3 L28 Q38 11678 Z3 L28 Q39 11679 Z3 L28 Q40 11680 Z3 L28 Q41 11681 Z3 L28 Q42 11682 Z3 L28 Q43 11683 Z3 L28 Q44 11684 Z3 L28 Q45 11685 Z3 L28 Q46 11686 Z3 L28 Q47 11687 Z3 L28 Q48 11688 Z3 L28 Q49 11689 Z3 L28 Q50 11690 Z3 L28 Q51 11691 Z3 L28 Q52 11692 Z3 L28 Q53 11693 Z3 L28 Q54 11694 Z3 L28 Q55 11695 Z3 L28 Q56 11696 Z3 L28 Q57 11697 Z3 L28 Q58 11698 Z3 L28 Q59 11699 Z3 L28 Q60 11700 Z3 L28 Q61 11701 Z3 L28 Q62 11702 Z3 L28 Q63 11703 Z3 L28 Q64 11704 Z3 L28 Q65 11705 Z3 L28 Q66 11706 Z3 L28 Q67 11707 Z3 L28 Q68 11708 Z3 L28 Q69 11709 Z3 L28 Q70 11710 Z3 L28 Q71 11711 Z3 L28 Q72 11712 Z3 L28 Q73 11713 Z3 L28 Q74 11714 Z3 L28 Q75 11715 Z3 L28 Q76 11716 Z3 L28 Q77 11717 Z3 L28 Q78 11718 Z3 L28 Q79 11719 Z3 L28 Q80 11720 Z3 L28 Q81 11721 Z3 L28 Q82 11722 Z3 L28 Q83 11723 Z3 L28 Q84 11724 Z3 L28 Q85 11725 Z3 L28 Q86 11726 Z3 L28 Q87 11727 Z3 L28 Q88 11728 Z3 L28 Q89 11729 Z3 L28 Q90 11730 Z3 L28 Q91 11731 Z3 L28 Q92 11732 Z3 L28 Q93 11733 Z3 L28 Q94 11734 Z3 L28 Q95 11735 Z3 L28 Q96 11736 Z3 L28 Q97 11737 Z3 L28 Q98 11738 Z3 L28 Q99 11739 Z3 L28 Q100 11740 Z3 L28 Q101 11741 Z3 L28 Q102 11742 Z3 L28 Q103 11743 Z3 L29 Q1 11744 Z3 L29 Q2 11745 Z3 L29 Q3 11746 Z3 L29 Q4 11747 Z3 L29 Q5 11748 Z3 L29 Q6 11749 Z3 L29 Q7 11750 Z3 L29 Q8 11751 Z3 L29 Q9 11752 Z3 L29 Q10 11753 Z3 L29 Q11 11754 Z3 L29 Q12 11755 Z3 L29 Q13 11756 Z3 L29 Q14 11757 Z3 L29 Q15 11758 Z3 L29 Q16 11759 Z3 L29 Q17 11760 Z3 L29 Q18 11761 Z3 L29 Q19 11762 Z3 L29 Q20 11763 Z3 L29 Q21 11764 Z3 L29 Q22 11765 Z3 L29 Q23 11766 Z3 L29 Q24 11767 Z3 L29 Q25 11768 Z3 L29 Q26 11769 Z3 L29 Q27 11770 Z3 L29 Q28 11771 Z3 L29 Q29 11772 Z3 L29 Q30 11773 Z3 L29 Q31 11774 Z3 L29 Q32 11775 Z3 L29 Q33 11776 Z3 L29 Q34 11777 Z3 L29 Q35 11778 Z3 L29 Q36 11779 Z3 L29 Q37 11780 Z3 L29 Q38 11781 Z3 L29 Q39 11782 Z3 L29 Q40 11783 Z3 L29 Q41 11784 Z3 L29 Q42 11785 Z3 L29 Q43 11786 Z3 L29 Q44 11787 Z3 L29 Q45 11788 Z3 L29 Q46 11789 Z3 L29 Q47 11790 Z3 L29 Q48 11791 Z3 L29 Q49 11792 Z3 L29 Q50 11793 Z3 L29 Q51 11794 Z3 L29 Q52 11795 Z3 L29 Q53 11796 Z3 L29 Q54 11797 Z3 L29 Q55 11798 Z3 L29 Q56 11799 Z3 L29 Q57 11800 Z3 L29 Q58 11801 Z3 L29 Q59 11802 Z3 L29 Q60 11803 Z3 L29 Q61 11804 Z3 L29 Q62 11805 Z3 L29 Q63 11806 Z3 L29 Q64 11807 Z3 L29 Q65 11808 Z3 L29 Q66 11809 Z3 L29 Q67 11810 Z3 L29 Q68 11811 Z3 L29 Q69 11812 Z3 L29 Q70 11813 Z3 L29 Q71 11814 Z3 L29 Q72 11815 Z3 L29 Q73 11816 Z3 L29 Q74 11817 Z3 L29 Q75 11818 Z3 L29 Q76 11819 Z3 L29 Q77 11820 Z3 L29 Q78 11821 Z3 L29 Q79 11822 Z3 L29 Q80 11823 Z3 L29 Q81 11824 Z3 L29 Q82 11825 Z3 L29 Q83 11826 Z3 L29 Q84 11827 Z3 L29 Q85 11828 Z3 L29 Q86 11829 Z3 L29 Q87 11830 Z3 L29 Q88 11831 Z3 L29 Q89

TABLE 1-65 11832 Z3 L29 Q90 11833 Z3 L29 Q91 11834 Z3 L29 Q92 11835 Z3 L29 Q93 11836 Z3 L29 Q94 11837 Z3 L29 Q95 11838 Z3 L29 Q96 11839 Z3 L29 Q97 11840 Z3 L29 Q98 11841 Z3 L29 Q99 11842 Z3 L29 Q100 11843 Z3 L29 Q101 11844 Z3 L29 Q102 11845 Z3 L29 Q103 11846 Z3 L30 Q1 11847 Z3 L30 Q2 11848 Z3 L30 Q3 11849 Z3 L30 Q4 11850 Z3 L30 Q5 11851 Z3 L30 Q6 11852 Z3 L30 Q7 11853 Z3 L30 Q8 11854 Z3 L30 Q9 11855 Z3 L30 Q10 11856 Z3 L30 Q11 11857 Z3 L30 Q12 11858 Z3 L30 Q13 11859 Z3 L30 Q14 11860 Z3 L30 Q15 11861 Z3 L30 Q16 11862 Z3 L30 Q17 11863 Z3 L30 Q18 11864 Z3 L30 Q19 11865 Z3 L30 Q20 11866 Z3 L30 Q21 11867 Z3 L30 Q22 11868 Z3 L30 Q23 11869 Z3 L30 Q24 11870 Z3 L30 Q25 11871 Z3 L30 Q26 11872 Z3 L30 Q27 11873 Z3 L30 Q28 11874 Z3 L30 Q29 11875 Z3 L30 Q30 11876 Z3 L30 Q31 11877 Z3 L30 Q32 11878 Z3 L30 Q33 11879 Z3 L30 Q34 11880 Z3 L30 Q35 11881 Z3 L30 Q36 11882 Z3 L30 Q37 11883 Z3 L30 Q38 11884 Z3 L30 Q39 11885 Z3 L30 Q40 11886 Z3 L30 Q41 11887 Z3 L30 Q42 11888 Z3 L30 Q43 11889 Z3 L30 Q44 11890 Z3 L30 Q45 11891 Z3 L30 Q46 11892 Z3 L30 Q47 11893 Z3 L30 Q48 11894 Z3 L30 Q49 11895 Z3 L30 Q50 11896 Z3 L30 Q51 11897 Z3 L30 Q52 11898 Z3 L30 Q53 11899 Z3 L30 Q54 11900 Z3 L30 Q55 11901 Z3 L30 Q56 11902 Z3 L30 Q57 11903 Z3 L30 Q58 11904 Z3 L30 Q59 11905 Z3 L30 Q60 11906 Z3 L30 Q61 11907 Z3 L30 Q62 11908 Z3 L30 Q63 11909 Z3 L30 Q64 11910 Z3 L30 Q65 11911 Z3 L30 Q66 11912 Z3 L30 Q67 11913 Z3 L30 Q68 11914 Z3 L30 Q69 11915 Z3 L30 Q70 11916 Z3 L30 Q71 11917 Z3 L30 Q72 11918 Z3 L30 Q73 11919 Z3 L30 Q74 11920 Z3 L30 Q75 11921 Z3 L30 Q76 11922 Z3 L30 Q77 11923 Z3 L30 Q78 11924 Z3 L30 Q79 11925 Z3 L30 Q80 11926 Z3 L30 Q81 11927 Z3 L30 Q82 11928 Z3 L30 Q83 11929 Z3 L30 Q84 11930 Z3 L30 Q85 11931 Z3 L30 Q86 11932 Z3 L30 Q87 11933 Z3 L30 Q88 11934 Z3 L30 Q89 11935 Z3 L30 Q90 11936 Z3 L30 Q91 11937 Z3 L30 Q92 11938 Z3 L30 Q93 11939 Z3 L30 Q94 11940 Z3 L30 Q95 11941 Z3 L30 Q96 11942 Z3 L30 Q97 11943 Z3 L30 Q98 11944 Z3 L30 Q99 11945 Z3 L30 Q100 11946 Z3 L30 Q101 11947 Z3 L30 Q102 11948 Z3 L30 Q103 11949 Z3 L31 Q1 11950 Z3 L31 Q2 11951 Z3 L31 Q3 11952 Z3 L31 Q4 11953 Z3 L31 Q5 11954 Z3 L31 Q6 11955 Z3 L31 Q7 11956 Z3 L31 Q8 11957 Z3 L31 Q9 11958 Z3 L31 Q10 11959 Z3 L31 Q11 11960 Z3 L31 Q12 11961 Z3 L31 Q13 11962 Z3 L31 Q14 11963 Z3 L31 Q15 11964 Z3 L31 Q16 11965 Z3 L31 Q17 11966 Z3 L31 Q18 11967 Z3 L31 Q19 11968 Z3 L31 Q20 11969 Z3 L31 Q21 11970 Z3 L31 Q22 11971 Z3 L31 Q23 11972 Z3 L31 Q24 11973 Z3 L31 Q25 11974 Z3 L31 Q26 11975 Z3 L31 Q27 11976 Z3 L31 Q28 11977 Z3 L31 Q29 11978 Z3 L31 Q30 11979 Z3 L31 Q31 11980 Z3 L31 Q32 11981 Z3 L31 Q33 11982 Z3 L31 Q34 11983 Z3 L31 Q35 11984 Z3 L31 Q36 11985 Z3 L31 Q37 11986 Z3 L31 Q38 11987 Z3 L31 Q39 11988 Z3 L31 Q40 11989 Z3 L31 Q41 11990 Z3 L31 Q42 11991 Z3 L31 Q43 11992 Z3 L31 Q44 11993 Z3 L31 Q45 11994 Z3 L31 Q46 11995 Z3 L31 Q47 11996 Z3 L31 Q48 11997 Z3 L31 Q49 11998 Z3 L31 Q50 11999 Z3 L31 Q51 12000 Z3 L31 Q52 12001 Z3 L31 Q53 12002 Z3 L31 Q54 12003 Z3 L31 Q55 12004 Z3 L31 Q56 12005 Z3 L31 Q57 12006 Z3 L31 Q58 12007 Z3 L31 Q59 12008 Z3 L31 Q60 12009 Z3 L31 Q61 12010 Z3 L31 Q62 12011 Z3 L31 Q63 12012 Z3 L31 Q64 12013 Z3 L31 Q65 12014 Z3 L31 Q66 12015 Z3 L31 Q67 12016 Z3 L31 Q68 12017 Z3 L31 Q69 12018 Z3 L31 Q70 12019 Z3 L31 Q71 12020 Z3 L31 Q72 12021 Z3 L31 Q73 12022 Z3 L31 Q74 12023 Z3 L31 Q75 12024 Z3 L31 Q76 12025 Z3 L31 Q77 12026 Z3 L31 Q78 12027 Z3 L31 Q79 12028 Z3 L31 Q80 12029 Z3 L31 Q81 12030 Z3 L31 Q82 12031 Z3 L31 Q83 12032 Z3 L31 Q84

TABLE 1-66 12033 Z3 L31 Q85 12034 Z3 L31 Q86 12035 Z3 L31 Q87 12036 Z3 L31 Q88 12037 Z3 L31 Q89 12038 Z3 L31 Q90 12039 Z3 L31 Q91 12040 Z3 L31 Q92 12041 Z3 L31 Q93 12042 Z3 L31 Q94 12043 Z3 L31 Q95 12044 Z3 L31 Q96 12045 Z3 L31 Q97 12046 Z3 L31 Q98 12047 Z3 L31 Q99 12048 Z3 L31 Q100 12049 Z3 L31 Q101 12050 Z3 L31 Q102 12051 Z3 L31 Q103 12052 Z3 L32 Q1 12053 Z3 L32 Q2 12054 Z3 L32 Q3 12055 Z3 L32 Q4 12056 Z3 L32 Q5 12057 Z3 L32 Q6 12058 Z3 L32 Q7 12059 Z3 L32 Q8 12060 Z3 L32 Q9 12061 Z3 L32 Q10 12062 Z3 L32 Q11 12063 Z3 L32 Q12 12064 Z3 L32 Q13 12065 Z3 L32 Q14 12066 Z3 L32 Q15 12067 Z3 L32 Q16 12068 Z3 L32 Q17 12069 Z3 L32 Q18 12070 Z3 L32 Q19 12071 Z3 L32 Q20 12072 Z3 L32 Q21 12073 Z3 L32 Q22 12074 Z3 L32 Q23 12075 Z3 L32 Q24 12076 Z3 L32 Q25 12077 Z3 L32 Q26 12078 Z3 L32 Q27 12079 Z3 L32 Q28 12080 Z3 L32 Q29 12081 Z3 L32 Q30 12082 Z3 L32 Q31 12083 Z3 L32 Q32 12084 Z3 L32 Q33 12085 Z3 L32 Q34 12086 Z3 L32 Q35 12087 Z3 L32 Q36 12088 Z3 L32 Q37 12089 Z3 L32 Q38 12090 Z3 L32 Q39 12091 Z3 L32 Q40 12092 Z3 L32 Q41 12093 Z3 L32 Q42 12094 Z3 L32 Q43 12095 Z3 L32 Q44 12096 Z3 L32 Q45 12097 Z3 L32 Q46 12098 Z3 L32 Q47 12099 Z3 L32 Q48 12100 Z3 L32 Q49 12101 Z3 L32 Q50 12102 Z3 L32 Q51 12103 Z3 L32 Q52 12104 Z3 L32 Q53 12105 Z3 L32 Q54 12106 Z3 L32 Q55 12107 Z3 L32 Q56 12108 Z3 L32 Q57 12109 Z3 L32 Q58 12110 Z3 L32 Q59 12111 Z3 L32 Q60 12112 Z3 L32 Q61 12113 Z3 L32 Q62 12114 Z3 L32 Q63 12115 Z3 L32 Q64 12116 Z3 L32 Q65 12117 Z3 L32 Q66 12118 Z3 L32 Q67 12119 Z3 L32 Q68 12120 Z3 L32 Q69 12121 Z3 L32 Q70 12122 Z3 L32 Q71 12123 Z3 L32 Q72 12124 Z3 L32 Q73 12125 Z3 L32 Q74 12126 Z3 L32 Q75 12127 Z3 L32 Q76 12128 Z3 L32 Q77 12129 Z3 L32 Q78 12130 Z3 L32 Q79 12131 Z3 L32 Q80 12132 Z3 L32 Q81 12133 Z3 L32 Q82 12134 Z3 L32 Q83 12135 Z3 L32 Q84 12136 Z3 L32 Q85 12137 Z3 L32 Q86 12138 Z3 L32 Q87 12139 Z3 L32 Q88 12140 Z3 L32 Q89 12141 Z3 L32 Q90 12142 Z3 L32 Q91 12143 Z3 L32 Q92 12144 Z3 L32 Q93 12145 Z3 L32 Q94 12146 Z3 L32 Q95 12147 Z3 L32 Q96 12148 Z3 L32 Q97 12149 Z3 L32 Q98 12150 Z3 L32 Q99 12151 Z3 L32 Q100 12152 Z3 L32 Q101 12153 Z3 L32 Q102 12154 Z3 L32 Q103 12155 Z3 L33 Q1 12156 Z3 L33 Q2 12157 Z3 L33 Q3 12158 Z3 L33 Q4 12159 Z3 L33 Q5 12160 Z3 L33 Q6 12161 Z3 L33 Q7 12162 Z3 L33 Q8 12163 Z3 L33 Q9 12164 Z3 L33 Q10 12165 Z3 L33 Q11 12166 Z3 L33 Q12 12167 Z3 L33 Q13 12168 Z3 L33 Q14 12169 Z3 L33 Q15 12170 Z3 L33 Q16 12171 Z3 L33 Q17 12172 Z3 L33 Q18 12173 Z3 L33 Q19 12174 Z3 L33 Q20 12175 Z3 L33 Q21 12176 Z3 L33 Q22 12177 Z3 L33 Q23 12178 Z3 L33 Q24 12179 Z3 L33 Q25 12180 Z3 L33 Q26 12181 Z3 L33 Q27 12182 Z3 L33 Q26 12183 Z3 L33 Q29 12184 Z3 L33 Q30 12185 Z3 L33 Q31 12186 Z3 L33 Q32 12187 Z3 L33 Q33 12188 Z3 L33 Q34 12189 Z3 L33 Q35 12190 Z3 L33 Q36 12191 Z3 L33 Q37 12192 Z3 L33 Q38 12193 Z3 L33 Q39 12194 Z3 L33 Q40 12195 Z3 L33 Q41 12196 Z3 L33 Q42 12197 Z3 L33 Q43 12198 Z3 L33 Q44 12199 Z3 L33 Q45 12200 Z3 L33 Q46 12201 Z3 L33 Q47 12202 Z3 L33 Q48 12203 Z3 L33 Q49 12204 Z3 L33 Q50 12205 Z3 L33 Q51 12206 Z3 L33 Q52 12207 Z3 L33 Q53 12208 Z3 L33 Q54 12209 Z3 L33 Q55 12210 Z3 L33 Q56 12211 Z3 L33 Q57 12212 Z3 L33 Q58 12213 Z3 L33 Q59 12214 Z3 L33 Q60 12215 Z3 L33 Q61 12216 Z3 L33 Q62 12217 Z3 L33 Q63 12218 Z3 L33 Q64 12219 Z3 L33 Q65 12220 Z3 L33 Q66 12221 Z3 L33 Q67 12222 Z3 L33 Q68 12223 Z3 L33 Q69 12224 Z3 L33 Q70 12225 Z3 L33 Q71 12226 Z3 L33 Q72 12227 Z3 L33 Q73 12228 Z3 L33 Q74 12229 Z3 L33 Q75 12230 Z3 L33 Q76 12231 Z3 L33 Q77 12232 Z3 L33 Q78 12233 Z3 L33 Q79

TABLE 1-67 12234 Z3 L33 Q80 12235 Z3 L33 Q81 12236 Z3 L33 Q82 12237 Z3 L33 Q83 12238 Z3 L33 Q84 12239 Z3 L33 Q85 12240 Z3 L33 Q86 12241 Z3 L33 Q87 12242 Z3 L33 Q88 12243 Z3 L33 Q89 12244 Z3 L33 Q90 12245 Z3 L33 Q91 12246 Z3 L33 Q92 12247 Z3 L33 Q93 12248 Z3 L33 Q94 12249 Z3 L33 Q95 12250 Z3 L33 Q96 12251 Z3 L33 Q97 12252 Z3 L33 Q98 12253 Z3 L33 Q99 12254 Z3 L33 Q100 12255 Z3 L33 Q101 12256 Z3 L33 Q102 12257 Z3 L33 Q103 12258 Z3 L34 Q1 12259 Z3 L34 Q2 12260 Z3 L34 Q3 12261 Z3 L34 Q4 12262 Z3 L34 Q5 12263 Z3 L34 Q6 12264 Z3 L34 Q7 12265 Z3 L34 Q8 12266 Z3 L34 Q9 12267 Z3 L34 Q10 12268 Z3 L34 Q11 12269 Z3 L34 Q12 12270 Z3 L34 Q13 12271 Z3 L34 Q14 12272 Z3 L34 Q15 12273 Z3 L34 Q16 12274 Z3 L34 Q17 12275 Z3 L34 Q18 12276 Z3 L34 Q19 12277 Z3 L34 Q20 12278 Z3 L34 Q21 12279 Z3 L34 Q22 12280 Z3 L34 Q23 12281 Z3 L34 Q24 12282 Z3 L34 Q25 12283 Z3 L34 Q26 12284 Z3 L34 Q27 12285 Z3 L34 Q28 12286 Z3 L34 Q29 12287 Z3 L34 Q30 12288 Z3 L34 Q31 12289 Z3 L34 Q32 12290 Z3 L34 Q33 12291 Z3 L34 Q34 12292 Z3 L34 Q35 12293 Z3 L34 Q36 12294 Z3 L34 Q37 12295 Z3 L34 Q38 12296 Z3 L34 Q39 12297 Z3 L34 Q40 12298 Z3 L34 Q41 12299 Z3 L34 Q42 12300 Z3 L34 Q43 12301 Z3 L34 Q44 12302 Z3 L34 Q45 12303 Z3 L34 Q46 12304 Z3 L34 Q47 12305 Z3 L34 Q48 12306 Z3 L34 Q49 12307 Z3 L34 Q50 12308 Z3 L34 Q51 12309 Z3 L34 Q52 12310 Z3 L34 Q53 12311 Z3 L34 Q54 12312 Z3 L34 Q55 12313 Z3 L34 Q56 12314 Z3 L34 Q57 12315 Z3 L34 Q58 12316 Z3 L34 Q59 12317 Z3 L34 Q60 12318 Z3 L34 Q61 12319 Z3 L34 Q62 12320 Z3 L34 Q63 12321 Z3 L34 Q64 12322 Z3 L34 Q65 12323 Z3 L34 Q66 12324 Z3 L34 Q67 12325 Z3 L34 Q68 12326 Z3 L34 Q69 12327 Z3 L34 Q70 12328 Z3 L34 Q71 12329 Z3 L34 Q72 12330 Z3 L34 Q73 12331 Z3 L34 Q74 12332 Z3 L34 Q75 12333 Z3 L34 Q76 12334 Z3 L34 Q77 12335 Z3 L34 Q78 12336 Z3 L34 Q79 12337 Z3 L34 Q80 12338 Z3 L34 Q81 12339 Z3 L34 Q82 12340 Z3 L34 Q83 12341 Z3 L34 Q84 12342 Z3 L34 Q85 12343 Z3 L34 Q86 12344 Z3 L34 Q87 12345 Z3 L34 Q88 12346 Z3 L34 Q89 12347 Z3 L34 Q90 12348 Z3 L34 Q91 12349 Z3 L34 Q92 12350 Z3 L34 Q93 12351 Z3 L34 Q94 12352 Z3 L34 Q95 12353 Z3 L34 Q96 12354 Z3 L34 Q97 12355 Z3 L34 Q98 12356 Z3 L34 Q99 12357 Z3 L34 Q100 12358 Z3 L34 Q101 12359 Z3 L34 Q102 12360 Z3 L34 Q103 12361 Z3 L35 Q1 12362 Z3 L35 Q2 12363 Z3 L35 Q3 12364 Z3 L35 Q4 12365 Z3 L35 Q5 12366 Z3 L35 Q6 12367 Z3 L35 Q7 12368 Z3 L35 Q8 12369 Z3 L35 Q9 12370 Z3 L35 Q10 12371 Z3 L35 Q11 12372 Z3 L35 Q12 12373 Z3 L35 Q13 12374 Z3 L35 Q14 12375 Z3 L35 Q15 12376 Z3 L35 Q16 12377 Z3 L35 Q17 12378 Z3 L35 Q18 12379 Z3 L35 Q19 12380 Z3 L35 Q20 12381 Z3 L35 Q21 12382 Z3 L35 Q22 12383 Z3 L35 Q23 12384 Z3 L35 Q24 12385 Z3 L35 Q25 12386 Z3 L35 Q26 12387 Z3 L35 Q27 12388 Z3 L35 Q28 12389 Z3 L35 Q29 12390 Z3 L35 Q30 12391 Z3 L35 Q31 12392 Z3 L35 Q32 12393 Z3 L35 Q33 12394 Z3 L35 Q34 12395 Z3 L35 Q35 12396 Z3 L35 Q36 12397 Z3 L35 Q37 12398 Z3 L35 Q38 12399 Z3 L35 Q39 12400 Z3 L35 Q40 12401 Z3 L35 Q41 12402 Z3 L35 Q42 12403 Z3 L35 Q43 12404 Z3 L35 Q44 12405 Z3 L35 Q45 12406 Z3 L35 Q46 12407 Z3 L35 Q47 12408 Z3 L35 Q48 12409 Z3 L35 Q49 12410 Z3 L35 Q50 12411 Z3 L35 Q51 12412 Z3 L35 Q52 12413 Z3 L35 Q53 12414 Z3 L35 Q54 12415 Z3 L35 Q55 12416 Z3 L35 Q56 12417 Z3 L35 Q57 12418 Z3 L35 Q58 12419 Z3 L35 Q59 12420 Z3 L35 Q60 12421 Z3 L35 Q61 12422 Z3 L35 Q62 12423 Z3 L35 Q63 12424 Z3 L35 Q64 12425 Z3 L35 Q65 12426 Z3 L35 Q66 12427 Z3 L35 Q67 12428 Z3 L35 Q68 12429 Z3 L35 Q69 12430 Z3 L35 Q70 12431 Z3 L35 Q71 12432 Z3 L35 Q72 12433 Z3 L35 Q73 12434 Z3 L35 Q74

TABLE 1-68 12435 Z3 L35 Q75 12436 Z3 L35 Q76 12437 Z3 L35 Q77 12438 Z3 L35 Q78 12439 Z3 L35 Q79 12440 Z3 L35 Q80 12441 Z3 L35 Q81 12442 Z3 L35 Q82 12443 Z3 L35 Q83 12444 Z3 L35 Q84 12445 Z3 L35 Q85 12446 Z3 L35 Q86 12447 Z3 L35 Q87 12448 Z3 L35 Q88 12449 Z3 L35 Q89 12450 Z3 L35 Q90 12451 Z3 L35 Q91 12452 Z3 L35 Q92 12453 Z3 L35 Q93 12454 Z3 L35 Q94 12455 Z3 L35 Q95 12456 Z3 L35 Q96 12457 Z3 L35 Q97 12458 Z3 L35 Q98 12459 Z3 L35 Q99 12460 Z3 L35 Q100 12461 Z3 L35 Q101 12462 Z3 L35 Q102 12463 Z3 L35 Q103 12464 Z3 L36 Q1 12465 Z3 L36 Q2 12466 Z3 L36 Q3 12467 Z3 L36 Q4 12468 Z3 L36 Q5 12469 Z3 L36 Q6 12470 Z3 L36 Q7 12471 Z3 L36 Q8 12472 Z3 L36 Q9 12473 Z3 L36 Q10 12474 Z3 L36 Q11 12475 Z3 L36 Q12 12476 Z3 L36 Q13 12477 Z3 L36 Q14 12478 Z3 L36 Q15 12479 Z3 L36 Q16 12480 Z3 L36 Q17 12481 Z3 L36 Q18 12482 Z3 L36 Q19 12483 Z3 L36 Q20 12484 Z3 L36 Q21 12485 Z3 L36 Q22 12486 Z3 L36 Q23 12487 Z3 L36 Q24 12488 Z3 L36 Q25 12489 Z3 L36 Q26 12490 Z3 L36 Q27 12491 Z3 L36 Q28 12492 Z3 L36 Q29 12493 Z3 L36 Q30 12494 Z3 L36 Q31 12495 Z3 L36 Q32 12496 Z3 L36 Q33 12497 Z3 L36 Q34 12498 Z3 L36 Q35 12499 Z3 L36 Q36 12500 Z3 L36 Q37 12501 Z3 L36 Q38 12502 Z3 L36 Q39 12503 Z3 L36 Q40 12504 Z3 L36 Q41 12505 Z3 L36 Q42 12506 Z3 L36 Q43 12507 Z3 L36 Q44 12508 Z3 L36 Q45 12509 Z3 L36 Q46 12510 Z3 L36 Q47 12511 Z3 L36 Q48 12512 Z3 L36 Q49 12513 Z3 L36 Q50 12514 Z3 L36 Q51 12515 Z2 L36 Q52 12516 Z3 L36 Q53 12517 Z3 L36 Q54 12518 Z3 L36 Q55 12519 Z3 L36 Q56 12520 Z3 L36 Q57 12521 Z3 L36 Q58 12522 Z3 L36 Q59 12523 Z3 L36 Q60 12524 Z3 L36 Q61 12525 Z3 L36 Q62 12526 Z3 L36 Q63 12527 Z3 L36 Q64 12528 Z3 L36 Q65 12529 Z3 L36 Q66 12530 Z3 L36 Q67 12531 Z3 L36 Q68 12532 Z3 L36 Q69 12533 Z3 L36 Q70 12534 Z3 L36 Q71 12535 Z3 L36 Q72 12536 Z3 L36 Q73 12537 Z3 L36 Q74 12538 Z3 L36 Q75 12539 Z3 L36 Q76 12540 Z3 L36 Q77 12541 Z3 L36 Q78 12542 Z3 L36 Q79 12543 Z3 L36 Q80 12544 Z3 L36 Q81 12545 Z3 L36 Q82 12546 Z3 L36 Q83 12547 Z3 L36 Q84 12548 Z3 L36 Q85 12549 Z3 L36 Q86 12550 Z3 L36 Q87 12551 Z3 L36 Q88 12552 Z3 L36 Q89 12553 Z3 L36 Q90 12554 Z3 L36 Q91 12555 Z3 L36 Q92 12556 Z3 L36 Q93 12557 Z3 L36 Q94 12558 Z3 L36 Q95 12559 Z3 L36 Q96 12560 Z3 L36 Q97 12561 Z3 L36 Q98 12562 Z3 L36 Q99 12563 Z3 L36 Q100 12564 Z3 L36 Q101 12565 Z3 L36 Q102 12566 Z3 L36 Q103 12567 Z4 L15 Q1 12568 Z4 L15 Q2 12569 Z4 L15 Q3 12570 Z4 L15 Q4 12571 Z4 L15 Q5 12572 Z4 L15 Q6 12573 Z4 L15 Q7 12574 Z4 L15 Q8 12575 Z4 L15 Q9 12576 Z4 L15 Q10 12577 Z4 L15 Q11 12578 Z4 L15 Q12 12579 Z4 L15 Q13 12580 Z4 L15 Q14 12581 Z4 L15 Q15 12582 Z4 L15 Q16 12583 Z4 L15 Q17 12584 Z4 L15 Q18 12585 Z4 L15 Q19 12586 Z4 L15 Q20 12587 Z4 L15 Q21 12588 Z4 L15 Q22 12589 Z4 L15 Q23 12590 Z4 L15 Q24 12591 Z4 L15 Q25 12592 Z4 L15 Q26 12593 Z4 L15 Q27 12594 Z4 L15 Q28 12595 Z4 L15 Q29 12596 Z4 L15 Q30 12597 Z4 L15 Q31 12598 Z4 L15 Q32 12599 Z4 L15 Q33 12600 Z4 L15 Q34 12601 Z4 L15 Q35 12602 Z4 L15 Q36 12603 Z4 L15 Q37 12604 Z4 L15 Q38 12605 Z4 L15 Q39 12606 Z4 L15 Q40 12607 Z4 L15 Q41 12608 Z4 L15 Q42 12609 Z4 L15 Q43 12610 Z4 L15 Q44 12611 Z4 L15 Q45 12612 Z4 L15 Q46 12613 Z4 L15 Q47 12614 Z4 L15 Q48 12615 Z4 L15 Q49 12616 Z4 L15 Q50 12617 Z4 L15 Q51 12618 Z4 L15 Q52 12619 Z4 L15 Q53 12620 Z4 L15 Q54 12621 Z4 L15 Q55 12622 Z4 L15 Q56 12623 Z4 L15 Q57 12624 Z4 L15 Q58 12625 Z4 L15 Q59 12626 Z4 L15 Q60 12627 Z4 L15 Q61 12628 Z4 L15 Q62 12629 Z4 L15 Q63 12630 Z4 L15 Q64 12631 Z4 L15 Q65 12632 Z4 L15 Q66 12633 Z4 L15 Q67 12634 Z4 L15 Q68 12635 Z4 L15 Q69

TABLE 1-69 12636 Z4 L15 Q70 12637 Z4 L15 Q71 12638 Z4 L15 Q72 12639 Z4 L15 Q73 12640 Z4 L15 Q74 12641 Z4 L15 Q75 12642 Z4 L15 Q76 12643 Z4 L15 Q77 12644 Z4 L15 Q78 12645 Z4 L15 Q79 12646 Z4 L15 Q80 12647 Z4 L15 Q81 12648 Z4 L15 Q82 12649 Z4 L15 Q83 12650 Z4 L15 Q84 12651 Z4 L15 Q85 12652 Z4 L15 Q86 12653 Z4 L15 Q87 12654 Z4 L15 Q88 12655 Z4 L15 Q89 12656 Z4 L15 Q90 12657 Z4 L15 Q91 12658 Z4 L15 Q92 12659 Z4 L15 Q93 12660 Z4 L15 Q94 12661 Z4 L15 Q95 12662 Z4 L15 Q96 12663 Z4 L15 Q97 12664 Z4 L15 Q98 12665 Z4 L15 Q99 12666 Z4 L15 Q100 12667 Z4 L15 Q101 12668 Z4 L15 Q102 12669 Z4 L15 Q103 12670 Z4 L16 Q1 12671 Z4 L16 Q2 12672 Z4 L16 Q3 12673 Z4 L16 Q4 12674 Z4 L16 Q5 12675 Z4 L16 Q6 12676 Z4 L16 Q7 12677 Z4 L16 Q8 12678 Z4 L16 Q9 12679 Z4 L16 Q10 12680 Z4 L16 Q11 12681 Z4 L16 Q12 12682 Z4 L16 Q13 12683 Z4 L16 Q14 12684 Z4 L16 Q15 12685 Z4 L16 Q16 12686 Z4 L16 Q17 12687 Z4 L16 Q18 12688 Z4 L16 Q19 12689 Z4 L16 Q20 12690 Z4 L16 Q21 12691 Z4 L16 Q22 12692 Z4 L16 Q23 12693 Z4 L16 Q24 12694 Z4 L16 Q25 12695 Z4 L16 Q26 12696 Z4 L16 Q27 12697 Z4 L16 Q28 12698 Z4 L16 Q29 12699 Z4 L16 Q30 12700 Z4 L16 Q31 12701 Z4 L16 Q32 12702 Z4 L16 Q33 12703 Z4 L16 Q34 12704 Z4 L16 Q35 12705 Z4 L16 Q36 12706 Z4 L16 Q37 12707 Z4 L16 Q38 12708 Z4 L16 Q39 12709 Z4 L16 Q40 12710 Z4 L16 Q41 12711 Z4 L16 Q42 12712 Z4 L16 Q43 12713 Z4 L16 Q44 12714 Z4 L16 Q45 12715 Z4 L16 Q46 12716 Z4 L16 Q47 12717 Z4 L16 Q48 12718 Z4 L16 Q49 12719 Z4 L16 Q50 12720 Z4 L16 Q51 12721 Z4 L16 Q52 12722 Z4 L16 Q53 12723 Z4 L16 Q54 12724 Z4 L16 Q55 12725 Z4 L16 Q56 12726 Z4 L16 Q57 12727 Z4 L16 Q58 12728 Z4 L16 Q59 12729 Z4 L16 Q60 12730 Z4 L16 Q61 12731 Z4 L16 Q62 12732 Z4 L16 Q63 12733 Z4 L16 Q64 12734 Z4 L16 Q65 12735 Z4 L16 Q66 12736 Z4 L16 Q67 12737 Z4 L16 Q68 12738 Z4 L16 Q69 12739 Z4 L16 Q70 12740 Z4 L16 Q71 12741 Z4 L16 Q72 12742 Z4 L16 Q73 12743 Z4 L16 Q74 12744 Z4 L16 Q75 12745 Z4 L16 Q76 12746 Z4 L16 Q77 12747 Z4 L16 Q78 12748 Z4 L16 Q79 12749 Z4 L16 Q80 12750 Z4 L16 Q81 12751 Z4 L16 Q82 12752 Z4 L16 Q83 12753 Z4 L16 Q84 12754 Z4 L16 Q85 12755 Z4 L16 Q86 12756 Z4 L16 Q87 12757 Z4 L16 Q88 12758 Z4 L16 Q89 12759 Z4 L16 Q90 12760 Z4 L16 Q91 12761 Z4 L16 Q92 12762 Z4 L16 Q93 12763 Z4 L16 Q94 12764 Z4 L16 Q95 12765 Z4 L16 Q96 12766 Z4 L16 Q97 12767 Z4 L16 Q98 12768 Z4 L16 Q99 12769 Z4 L16 Q100 12770 Z4 L16 Q101 12771 Z4 L16 Q102 12772 Z4 L16 Q103 12773 Z4 L17 Q1 12774 Z4 L17 Q2 12775 Z4 L17 Q3 12776 Z4 L17 Q4 12777 Z4 L17 Q5 12778 Z4 L17 Q6 12779 Z4 L17 Q7 12780 Z4 L17 Q8 12781 Z4 L17 Q9 12782 Z4 L17 Q10 12783 Z4 L17 Q11 12784 Z4 L17 Q12 12785 Z4 L17 Q13 12786 Z4 L17 Q14 12787 Z4 L17 Q15 12788 Z4 L17 Q16 12789 Z4 L17 Q17 12790 Z4 L17 Q18 12791 Z4 L17 Q19 12792 Z4 L17 Q20 12793 Z4 L17 Q21 12794 Z4 L17 Q22 12795 Z4 L17 Q23 12796 Z4 L17 Q24 12797 Z4 L17 Q25 12798 Z4 L17 Q26 12799 Z4 L17 Q27 12800 Z4 L17 Q28 12801 Z4 L17 Q29 12802 Z4 L17 Q30 12803 Z4 L17 Q31 12804 Z4 L17 Q32 12805 Z4 L17 Q33 12806 Z4 L17 Q34 12807 Z4 L17 Q35 12808 Z4 L17 Q36 12809 Z4 L17 Q37 12810 Z4 L17 Q38 12811 Z4 L17 Q39 12812 Z4 L17 Q40 12813 Z4 L17 Q41 12814 Z4 L17 Q42 12815 Z4 L17 Q43 12816 Z4 L17 Q44 12817 Z4 L17 Q45 12818 Z4 L17 Q46 12819 Z4 L17 Q47 12820 Z4 L17 Q48 12821 Z4 L17 Q49 12822 Z4 L17 Q50 12823 Z4 L17 Q51 12824 Z4 L17 Q52 12825 Z4 L17 Q53 12826 Z4 L17 Q54 12827 Z4 L17 Q55 12828 Z4 L17 Q56 12829 Z4 L17 Q57 12830 Z4 L17 Q58 12831 Z4 L17 Q59 12832 Z4 L17 Q60 12833 Z4 L17 Q61 12834 Z4 L17 Q62 12835 Z4 L17 Q63 12836 Z4 L17 Q64

TABLE 1-70 12837 Z4 L17 Q65 12838 Z4 L17 Q66 12839 Z4 L17 Q67 12840 Z4 L17 Q68 12841 Z4 L17 Q69 12842 Z4 L17 Q70 12843 Z4 L17 Q71 12844 Z4 L17 Q72 12845 Z4 L17 Q73 12846 Z4 L17 Q74 12847 Z4 L17 Q75 12848 Z4 L17 Q76 12849 Z4 L17 Q77 12850 Z4 L17 Q78 12851 Z4 L17 Q79 12852 Z4 L17 Q80 12853 Z4 L17 Q81 12854 Z4 L17 Q82 12855 Z4 L17 Q83 12856 Z4 L17 Q84 12857 Z4 L17 Q85 12858 Z4 L17 Q86 12859 Z4 L17 Q87 12860 Z4 L17 Q88 12861 Z4 L17 Q89 12862 Z4 L17 Q90 12863 Z4 L17 Q91 12864 Z4 L17 Q92 12865 Z4 L17 Q93 12866 Z4 L17 Q94 12867 Z4 L17 Q95 12868 Z4 L17 Q96 12869 Z4 L17 Q97 12870 Z4 L17 Q98 12871 Z4 L17 Q99 12872 Z4 L17 Q100 12873 Z4 L17 Q101 12874 Z4 L17 Q102 12875 Z4 L17 Q103 12876 Z4 L18 Q1 12877 Z4 L18 Q2 12878 Z4 L18 Q3 12879 Z4 L18 Q4 12880 Z4 L18 Q5 12881 Z4 L18 Q6 12882 Z4 L18 Q7 12883 Z4 L18 Q8 12884 Z4 L18 Q9 12885 Z4 L18 Q10 12886 Z4 L18 Q11 12887 Z4 L18 Q12 12888 Z4 L18 Q13 12889 Z4 L18 Q14 12890 Z4 L18 Q15 12891 Z4 L18 Q16 12892 Z4 L18 Q17 12893 Z4 L18 Q18 12894 Z4 L18 Q19 12895 Z4 L18 Q20 12896 Z4 L18 Q21 12897 Z4 L18 Q22 12898 Z4 L18 Q23 12899 Z4 L18 Q24 12900 Z4 L18 Q25 12901 Z4 L18 Q26 12902 Z4 L18 Q27 12903 Z4 L18 Q28 12904 Z4 L18 Q29 12905 Z4 L18 Q30 12906 Z4 L18 Q31 12907 Z4 L18 Q32 12908 Z4 L18 Q33 12909 Z4 L18 Q34 12910 Z4 L18 Q35 12911 Z4 L18 Q36 12912 Z4 L18 Q37 12913 Z4 L18 Q38 12914 Z4 L18 Q39 12915 Z4 L18 Q40 12916 Z4 L18 Q41 12917 Z4 L18 Q42 12918 Z4 L18 Q43 12919 Z4 L18 Q44 12920 Z4 L18 Q45 12921 Z4 L18 Q46 12922 Z4 L18 Q47 12923 Z4 L18 Q48 12924 Z4 L18 Q49 12925 Z4 L18 Q50 12926 Z4 L18 Q51 12927 Z4 L18 Q52 12928 Z4 L18 Q53 12929 Z4 L18 Q54 12930 Z4 L18 Q55 12931 Z4 L18 Q56 12932 Z4 L18 Q57 12933 Z4 L18 Q58 12934 Z4 L18 Q59 12935 Z4 L18 Q60 12936 Z4 L18 Q61 12937 Z4 L18 Q62 12938 Z4 L18 Q63 12939 Z4 L18 Q64 12940 Z4 L18 Q65 12941 Z4 L18 Q66 12942 Z4 L18 Q67 12943 Z4 L18 Q68 12944 Z4 L18 Q69 12945 Z4 L18 Q70 12946 Z4 L18 Q71 12947 Z4 L18 Q72 12948 Z4 L18 Q73 12949 Z4 L18 Q74 12950 Z4 L18 Q75 12951 Z4 L18 Q76 12952 Z4 L18 Q77 12953 Z4 L18 Q78 12954 Z4 L18 Q79 12955 Z4 L18 Q80 12956 Z4 L18 Q81 12957 Z4 L18 Q82 12958 Z4 L18 Q83 12959 Z4 L18 Q84 12960 Z4 L18 Q85 12961 Z4 L18 Q86 12962 Z4 L18 Q87 12963 Z4 L18 Q88 12964 Z4 L18 Q89 12965 Z4 L18 Q90 12966 Z4 L18 Q91 12967 Z4 L18 Q92 12968 Z4 L18 Q93 12969 Z4 L18 Q94 12970 Z4 L18 Q95 12971 Z4 L18 Q96 12972 Z4 L18 Q97 12973 Z4 L18 Q98 12974 Z4 L18 Q99 12975 Z4 L18 Q100 12976 Z4 L18 Q101 12977 Z4 L18 Q102 12978 Z4 L18 Q103 12979 Z4 L19 Q1 12980 Z4 L19 Q2 12981 Z4 L19 Q3 12982 Z4 L19 Q4 12983 Z4 L19 Q5 12984 Z4 L19 Q6 12985 Z4 L19 Q7 12986 Z4 L19 Q8 12987 Z4 L19 Q9 12988 Z4 L19 Q10 12989 Z4 L19 Q11 12990 Z4 L19 Q12 12991 Z4 L19 Q13 12992 Z4 L19 Q14 12993 Z4 L19 Q15 12994 Z4 L19 Q16 12995 Z4 L19 Q17 12996 Z4 L19 Q18 12997 Z4 L19 Q19 12998 Z4 L19 Q20 12999 Z4 L19 Q21 13000 Z4 L19 Q22 13001 Z4 L19 Q23 13002 Z4 L19 Q24 13003 Z4 L19 Q25 13004 Z4 L19 Q26 13005 Z4 L19 Q27 13006 Z4 L19 Q28 13007 Z4 L19 Q29 13008 Z4 L19 Q30 13009 Z4 L19 Q31 13010 Z4 L19 Q32 13011 Z4 L19 Q33 13012 Z4 L19 Q34 13013 Z4 L19 Q35 13014 Z4 L19 Q36 13015 Z4 L19 Q37 13016 Z4 L19 Q38 13017 Z4 L19 Q39 13018 Z4 L19 Q40 13019 Z4 L19 Q41 13020 Z4 L19 Q42 13021 Z4 L19 Q43 13022 Z4 L19 Q44 13023 Z4 L19 Q45 13024 Z4 L19 Q46 13025 Z4 L19 Q47 13026 Z4 L19 Q48 13027 Z4 L19 Q49 13028 Z4 L19 Q50 13029 Z4 L19 Q51 13030 Z4 L19 Q52 13031 Z4 L19 Q53 13032 Z4 L19 Q54 13033 Z4 L19 Q55 13034 Z4 L19 Q56 13035 Z4 L19 Q57 13036 Z4 L19 Q58 13037 Z4 L19 Q59

TABLE 1-71 13038 Z4 L19 Q60 13039 Z4 L19 Q61 13040 Z4 L19 Q62 13041 Z4 L19 Q63 13042 Z4 L19 Q64 13043 Z4 L19 Q65 13044 Z4 L19 Q66 13045 Z4 L19 Q67 13046 Z4 L19 Q68 13047 Z4 L19 Q69 13048 Z4 L19 Q70 13049 Z4 L19 Q71 13050 Z4 L19 Q72 13051 Z4 L19 Q73 13052 Z4 L19 Q74 13053 Z4 L19 Q75 13054 Z4 L19 Q76 13055 Z4 L19 Q77 13056 Z4 L19 Q78 13057 Z4 L19 Q79 13058 Z4 L19 Q80 13059 Z4 L19 Q81 13060 Z4 L19 Q82 13061 Z4 L19 Q83 13062 Z4 L19 Q84 13063 Z4 L19 Q85 13064 Z4 L19 Q86 13065 Z4 L19 Q87 13066 Z4 L19 Q88 13067 Z4 L19 Q89 13068 Z4 L19 Q90 13069 Z4 L19 Q91 13070 Z4 L19 Q92 13071 Z4 L19 Q93 13072 Z4 L19 Q94 13073 Z4 L19 Q95 13074 Z4 L19 Q96 13075 Z4 L19 Q97 13076 Z4 L19 Q98 13077 Z4 L19 Q99 13078 Z4 L19 Q100 13079 Z4 L19 Q101 13080 Z4 L19 Q102 13081 Z4 L19 Q103 13082 Z4 L20 Q1 13083 Z4 L20 Q2 13084 Z4 L20 Q3 13085 Z4 L20 Q4 13086 Z4 L20 Q5 13087 Z4 L20 Q6 13088 Z4 L20 Q7 13089 Z4 L20 Q8 13090 Z4 L20 Q9 13091 Z4 L20 Q10 13092 Z4 L20 Q11 13093 Z4 L20 Q12 13094 Z4 L20 Q13 13095 Z4 L20 Q14 13096 Z4 L20 Q15 13097 Z4 L20 Q16 13098 Z4 L20 Q17 13099 Z4 L20 Q18 13100 Z4 L20 Q19 13101 Z4 L20 Q20 13102 Z4 L20 Q21 13103 Z4 L20 Q22 13104 Z4 L20 Q23 13105 Z4 L20 Q24 13106 Z4 L20 Q25 13107 Z4 L20 Q26 13108 Z4 L20 Q27 13109 Z4 L20 Q28 13110 Z4 L20 Q29 13111 Z4 L20 Q30 13112 Z4 L20 Q31 13113 Z4 L20 Q32 13114 Z4 L20 Q33 13115 Z4 L20 Q34 13116 Z4 L20 Q35 13117 Z4 L20 Q36 13118 Z4 L20 Q37 13119 Z4 L20 Q38 13120 Z4 L20 Q39 13121 Z4 L20 Q40 13122 Z4 L20 Q41 13123 Z4 L20 Q42 13124 Z4 L20 Q43 13125 Z4 L20 Q44 13126 Z4 L20 Q45 13127 Z4 L20 Q46 13128 Z4 L20 Q47 13129 Z4 L20 Q48 13130 Z4 L20 Q49 13131 Z4 L20 Q50 13132 Z4 L20 Q51 13133 Z4 L20 Q52 13134 Z4 L20 Q53 13135 Z4 L20 Q54 13136 Z4 L20 Q55 13137 Z4 L20 Q56 13138 Z4 L20 Q57 13139 Z4 L20 Q58 13140 Z4 L20 Q59 13141 Z4 L20 Q60 13142 Z4 L20 Q61 13143 Z4 L20 Q62 13144 Z4 L20 Q63 13145 Z4 L20 Q64 13146 Z4 L20 Q65 13147 Z4 L20 Q66 13148 Z4 L20 Q67 13149 Z4 L20 Q68 13150 Z4 L20 Q69 13151 Z4 L20 Q70 13152 Z4 L20 Q71 13153 Z4 L20 Q72 13154 Z4 L20 Q73 13155 Z4 L20 Q74 13156 Z4 L20 Q75 13157 Z4 L20 Q76 13158 Z4 L20 Q77 13159 Z4 L20 Q78 13160 Z4 L20 Q79 13161 Z4 L20 Q80 13162 Z4 L20 Q81 13163 Z4 L20 Q82 13164 Z4 L20 Q83 13165 Z4 L20 Q84 13166 Z4 L20 Q85 13167 Z4 L20 Q86 13168 Z4 L20 Q87 13169 Z4 L20 Q88 13170 Z4 L20 Q89 13171 Z4 L20 Q90 13172 Z4 L20 Q91 13173 Z4 L20 Q92 13174 Z4 L20 Q93 13175 Z4 L20 Q94 13176 Z4 L20 Q95 13177 Z4 L20 Q96 13178 Z4 L20 Q97 13179 Z4 L20 Q98 13180 Z4 L20 Q99 13181 Z4 L20 Q100 13182 Z4 L20 Q101 13183 Z4 L20 Q102 13184 Z4 L20 Q103 13185 Z4 L21 Q1 13186 Z4 L21 Q2 13187 Z4 L21 Q3 13188 Z4 L21 Q4 13189 Z4 L21 Q5 13190 Z4 L21 Q6 13191 Z4 L21 Q7 13192 Z4 L21 Q8 13193 Z4 L21 Q9 13194 Z4 L21 Q10 13195 Z4 L21 Q11 13196 Z4 L21 Q12 13197 Z4 L21 Q13 13198 Z4 L21 Q14 13199 Z4 L21 Q15 13200 Z4 L21 Q16 13201 Z4 L21 Q17 13202 Z4 L21 Q18 13203 Z4 L21 Q19 13204 Z4 L21 Q20 13205 Z4 L21 Q21 13206 Z4 L21 Q22 13207 Z4 L21 Q23 13208 Z4 L21 Q24 13209 Z4 L21 Q25 13210 Z4 L21 Q26 13211 Z4 L21 Q27 13212 Z4 L21 Q28 13213 Z4 L21 Q29 13214 Z4 L21 Q30 13215 Z4 L21 Q31 13216 Z4 L21 Q32 13217 Z4 L21 Q33 13218 Z4 L21 Q34 13219 Z4 L21 Q35 13220 Z4 L21 Q36 13221 Z4 L21 Q37 13222 Z4 L21 Q38 13223 Z4 L21 Q39 13224 Z4 L21 Q40 13225 Z4 L21 Q41 13226 Z4 L21 Q42 13227 Z4 L21 Q43 13228 Z4 L21 Q44 13229 Z4 L21 Q45 13230 Z4 L21 Q46 13231 Z4 L21 Q47 13232 Z4 L21 Q48 13233 Z4 L21 Q49 13234 Z4 L21 Q50 13235 Z4 L21 Q51 13236 Z4 L21 Q52 13237 Z4 L21 Q53 13238 Z4 L21 Q54

TABLE 1-72 13239 Z4 L21 Q55 13240 Z4 L21 Q56 13241 Z4 L21 Q57 13242 Z4 L21 Q58 13243 Z4 L21 Q59 13244 Z4 L21 Q60 13245 Z4 L21 Q61 13246 Z4 L21 Q62 13247 Z4 L21 Q63 13248 Z4 L21 Q64 13249 Z4 L21 Q65 13250 Z4 L21 Q66 13251 Z4 L21 Q67 13252 Z4 L21 Q68 13253 Z4 L21 Q69 13254 Z4 L21 Q70 13255 Z4 L21 Q71 13256 Z4 L21 Q72 13257 Z4 L21 Q73 13258 Z4 L21 Q74 13259 Z4 L21 Q75 13260 Z4 L21 Q76 13261 Z4 L21 Q77 13262 Z4 L21 Q78 13263 Z4 L21 Q79 13264 Z4 L21 Q80 13265 Z4 L21 Q81 13266 Z4 L21 Q82 13267 Z4 L21 Q83 13268 Z4 L21 Q84 13269 Z4 L21 Q85 13270 Z4 L21 Q86 13271 Z4 L21 Q87 13272 Z4 L21 Q88 13273 Z4 L21 Q89 13274 Z4 L21 Q90 13275 Z4 L21 Q91 13276 Z4 L21 Q92 13277 Z4 L21 Q93 13278 Z4 L21 Q94 13279 Z4 L21 Q95 13280 Z4 L21 Q96 13281 Z4 L21 Q97 13282 Z4 L21 Q98 13283 Z4 L21 Q99 13284 Z4 L21 Q100 13285 Z4 L21 Q101 13286 Z4 L21 Q102 13287 Z4 L21 Q103 13288 Z4 L22 Q1 13289 Z4 L22 Q2 13290 Z4 L22 Q3 13291 Z4 L22 Q4 13292 Z4 L22 Q5 13293 Z4 L22 Q6 13294 Z4 L22 Q7 13295 Z4 L22 Q8 13296 Z4 L22 Q9 13297 Z4 L22 Q10 13298 Z4 L22 Q11 13299 Z4 L22 Q12 13300 Z4 L22 Q13 13301 Z4 L22 Q14 13302 Z4 L22 Q15 13303 Z4 L22 Q16 13304 Z4 L22 Q17 13305 Z4 L22 Q18 13306 Z4 L22 Q19 13307 Z4 L22 Q20 13308 Z4 L22 Q21 13309 Z4 L22 Q22 13310 Z4 L22 Q23 13311 Z4 L22 Q24 13312 Z4 L22 Q25 13313 Z4 L22 Q26 13314 Z4 L22 Q27 13315 Z4 L22 Q28 13316 Z4 L22 Q29 13317 Z4 L22 Q30 13318 Z4 L22 Q31 13319 Z4 L22 Q32 13320 Z4 L22 Q33 13321 Z4 L22 Q34 13322 Z4 L22 Q35 13323 Z4 L22 Q36 13324 Z4 L22 Q37 13325 Z4 L22 Q38 13326 Z4 L22 Q39 13327 Z4 L22 Q40 13328 Z4 L22 Q41 13329 Z4 L22 Q42 13330 Z4 L22 Q43 13331 Z4 L22 Q44 13332 Z4 L22 Q45 13333 Z4 L22 Q46 13334 Z4 L22 Q47 13335 Z4 L22 Q48 13336 Z4 L22 Q49 13337 Z4 L22 Q50 13338 Z4 L22 Q51 13339 Z4 L22 Q52 13340 Z4 L22 Q53 13341 Z4 L22 Q54 13342 Z4 L22 Q55 13343 Z4 L22 Q56 13344 Z4 L22 Q57 13345 Z4 L22 Q58 13346 Z4 L22 Q59 13347 Z4 L22 Q60 13348 Z4 L22 Q61 13349 Z4 L22 Q62 13350 Z4 L22 Q63 13351 Z4 L22 Q64 13352 Z4 L22 Q65 13353 Z4 L22 Q66 13354 Z4 L22 Q67 13355 Z4 L22 Q68 13356 Z4 L22 Q69 13357 Z4 L22 Q70 13358 Z4 L22 Q71 13359 Z4 L22 Q72 13360 Z4 L22 Q73 13361 Z4 L22 Q74 13362 Z4 L22 Q75 13363 Z4 L22 Q76 13364 Z4 L22 Q77 13365 Z4 L22 Q78 13366 Z4 L22 Q79 13367 Z4 L22 Q80 13368 Z4 L22 Q81 13369 Z4 L22 Q82 13370 Z4 L22 Q83 13371 Z4 L22 Q84 13372 Z4 L22 Q85 13373 Z4 L22 Q86 13374 Z4 L22 Q87 13375 Z4 L22 Q88 13376 Z4 L22 Q89 13377 Z4 L22 Q90 13378 Z4 L22 Q91 13379 Z4 L22 Q92 13380 Z4 L22 Q93 13381 Z4 L22 Q94 13382 Z4 L22 Q95 13383 Z4 L22 Q96 13384 Z4 L22 Q97 13385 Z4 L22 Q98 13386 Z4 L22 Q99 13387 Z4 L22 Q100 13388 Z4 L22 Q101 13389 Z4 L22 Q102 13390 Z4 L22 Q103 13391 Z4 L23 Q1 13392 Z4 L23 Q2 13393 Z4 L23 Q3 13394 Z4 L23 Q4 13395 Z4 L23 Q5 13396 Z4 L23 Q6 13397 Z4 L23 Q7 13398 Z4 L23 Q8 13399 Z4 L23 Q9 13400 Z4 L23 Q10 13401 Z4 L23 Q11 13402 Z4 L23 Q12 13403 Z4 L23 Q13 13404 Z4 L23 Q14 13405 Z4 L23 Q15 13406 Z4 L23 Q16 13407 Z4 L23 Q17 13408 Z4 L23 Q18 13409 Z4 L23 Q19 13410 Z4 L23 Q20 13411 Z4 L23 Q21 13412 Z4 L23 Q22 13413 Z4 L23 Q23 13414 Z4 L23 Q24 13415 Z4 L23 Q25 13416 Z4 L23 Q26 13417 Z4 L23 Q27 13418 Z4 L23 Q28 13419 Z4 L23 Q29 13420 Z4 L23 Q30 13421 Z4 L23 Q31 13422 Z4 L23 Q32 13423 Z4 L23 Q33 13424 Z4 L23 Q34 13425 Z4 L23 Q35 13426 Z4 L23 Q36 13427 Z4 L23 Q37 13428 Z4 L23 Q38 13429 Z4 L23 Q39 13430 Z4 L23 Q40 13431 Z4 L23 Q41 13432 Z4 L23 Q42 13433 Z4 L23 Q43 13434 Z4 L23 Q44 13435 Z4 L23 Q45 13436 Z4 L23 Q46 13437 Z4 L23 Q47 13438 Z4 L23 Q48 13439 Z4 L23 Q49

TABLE 1-73 13440 Z4 L23 Q50 13441 Z4 L23 Q51 13442 Z4 L23 Q52 13443 Z4 L23 Q53 13444 Z4 L23 Q54 13445 Z4 L23 Q55 13446 Z4 L23 Q56 13447 Z4 L23 Q57 13448 Z4 L23 Q56 13449 Z4 L23 Q59 13450 Z4 L23 Q60 13451 Z4 L23 Q61 13452 Z4 L23 Q62 13453 Z4 L23 Q63 13454 Z4 L23 Q64 13455 Z4 L23 Q65 13456 Z4 L23 Q66 13457 Z4 L23 Q67 13458 Z4 L23 Q68 13459 Z4 L23 Q69 13460 Z4 L23 Q70 13461 Z4 L23 Q71 13462 Z4 L23 Q72 13463 Z4 L23 Q73 13464 Z4 L23 Q74 13465 Z4 L23 Q75 13466 Z4 L23 Q76 13467 Z4 L23 Q77 13468 Z4 L23 Q78 13469 Z4 L23 Q79 13470 Z4 L23 Q80 13471 Z4 L23 Q81 13472 Z4 L23 Q82 13473 Z4 L23 Q83 13474 Z4 L23 Q84 13475 Z4 L23 Q85 13476 Z4 L23 Q86 13477 Z4 L23 Q87 13478 Z4 L23 Q88 13479 Z4 L23 Q89 13480 Z4 L23 Q90 13481 Z4 L23 Q91 13482 Z4 L23 Q92 13483 Z4 L23 Q93 13484 Z4 L23 Q94 13485 Z4 L23 Q95 13486 Z4 L23 Q96 13487 Z4 L23 Q97 13488 Z4 L23 Q98 13489 Z4 L23 Q99 13490 Z4 L23 Q100 13491 Z4 L23 Q101 13492 Z4 L23 Q102 13493 Z4 L23 Q103 13494 Z4 L24 Q1 13495 Z4 L24 Q2 13496 Z4 L24 Q3 13497 Z4 L24 Q4 13498 Z4 L24 Q5 13499 Z4 L24 Q6 13500 Z4 L24 Q7 13501 Z4 L24 Q8 13502 Z4 L24 Q9 13503 Z4 L24 Q10 13504 Z4 L24 Q11 13505 Z4 L24 Q12 13506 Z4 L24 Q13 13507 Z4 L24 Q14 13508 Z4 L24 Q15 13509 Z4 L24 Q16 13510 Z4 L24 Q17 13511 Z4 L24 Q18 13512 Z4 L24 Q19 13513 Z4 L24 Q20 13514 Z4 L24 Q21 13515 Z4 L24 Q22 13516 Z4 L24 Q23 13517 Z4 L24 Q24 13518 Z4 L24 Q25 13519 Z4 L24 Q26 13520 Z4 L24 Q27 13521 Z4 L24 Q28 13522 Z4 L24 Q29 13523 Z4 L24 Q30 13524 Z4 L24 Q31 13525 Z4 L24 Q32 13526 Z4 L24 Q33 13527 Z4 L24 Q34 13528 Z4 L24 Q35 13529 Z4 L24 Q36 13530 Z4 L24 Q37 13531 Z4 L24 Q38 13532 Z4 L24 Q39 13533 Z4 L24 Q40 13534 Z4 L24 Q41 13535 Z4 L24 Q42 13536 Z4 L24 Q43 13537 Z4 L24 Q44 13538 Z4 L24 Q45 13539 Z4 L24 Q46 13540 Z4 L24 Q47 13541 Z4 L24 Q48 13542 Z4 L24 Q49 13543 Z4 L24 Q50 13544 Z4 L24 Q51 13545 Z4 L24 Q52 13546 Z4 L24 Q53 13547 Z4 L24 Q54 13548 Z4 L24 Q55 13549 Z4 L24 Q56 13550 Z4 L24 Q57 13551 Z4 L24 Q58 13552 Z4 L24 Q59 13553 Z4 L24 Q60 13554 Z4 L24 Q61 13555 Z4 L24 Q62 13556 Z4 L24 Q63 13557 Z4 L24 Q64 13558 Z4 L24 Q65 13559 Z4 L24 Q66 13560 Z4 L24 Q67 13561 Z4 L24 Q68 13562 Z4 L24 Q69 13563 Z4 L24 Q70 13564 Z4 L24 Q71 13565 Z4 L24 Q72 13566 Z4 L24 Q73 13567 Z4 L24 Q74 13568 Z4 L24 Q75 13569 Z4 L24 Q76 13570 Z4 L24 Q77 13571 Z4 L24 Q78 13572 Z4 L24 Q79 13573 Z4 L24 Q80 13574 Z4 L24 Q81 13575 Z4 L24 Q82 13576 Z4 L24 Q83 13577 Z4 L24 Q84 13578 Z4 L24 Q85 13579 Z4 L24 Q86 13580 Z4 L24 Q87 13581 Z4 L24 Q88 13582 Z4 L24 Q89 13583 Z4 L24 Q90 13584 Z4 L24 Q91 13585 Z4 L24 Q92 13586 Z4 L24 Q93 13587 Z4 L24 Q94 13588 Z4 L24 Q95 13589 Z4 L24 Q96 13590 Z4 L24 Q97 13591 Z4 L24 Q98 13592 Z4 L24 Q99 13593 Z4 L24 Q100 13594 Z4 L24 Q101 13595 Z4 L24 Q102 13596 Z4 L24 Q103 13597 Z4 L25 Q1 13598 Z4 L25 Q2 13599 Z4 L25 Q3 13600 Z4 L25 Q4 13601 Z4 L25 Q5 13602 Z4 L25 Q6 13603 Z4 L25 Q7 13604 Z4 L25 Q8 13605 Z4 L25 Q9 13606 Z4 L25 Q10 13607 Z4 L25 Q11 13608 Z4 L25 Q12 13609 Z4 L25 Q13 13610 Z4 L25 Q14 13611 Z4 L25 Q15 13612 Z4 L25 Q16 13613 Z4 L25 Q17 13614 Z4 L25 Q18 13615 Z4 L25 Q19 13616 Z4 L25 Q20 13617 Z4 L25 Q21 13618 Z4 L25 Q22 13619 Z4 L25 Q23 13620 Z4 L25 Q24 13621 Z4 L25 Q25 13622 Z4 L25 Q26 13623 Z4 L25 Q27 13624 Z4 L25 Q28 13625 Z4 L25 Q29 13626 Z4 L25 Q30 13627 Z4 L25 Q31 13628 Z4 L25 Q32 13629 Z4 L25 Q33 13630 Z4 L25 Q34 13631 Z4 L25 Q35 13632 Z4 L25 Q36 13633 Z4 L25 Q37 13634 Z4 L25 Q38 13635 Z4 L25 Q39 13636 Z4 L25 Q40 13637 Z4 L25 Q41 13638 Z4 L25 Q42 13639 Z4 L25 Q43 13640 Z4 L25 Q44

TABLE 1-74 13641 Z4 L25 Q45 13642 Z4 L25 Q46 13643 Z4 L25 Q47 13644 Z4 L25 Q48 13645 Z4 L25 Q49 13646 Z4 L25 Q50 13647 Z4 L25 Q51 13648 Z4 L25 Q52 13649 Z4 L25 Q53 13650 Z4 L25 Q54 13651 Z4 L25 Q55 13652 Z4 L25 Q56 13653 Z4 L25 Q57 13654 Z4 L25 Q58 13655 Z4 L25 Q59 13656 Z4 L25 Q60 13657 Z4 L25 Q61 13658 Z4 L25 Q62 13659 Z4 L25 Q63 13660 Z4 L25 Q64 13661 Z4 L25 Q65 13662 Z4 L25 Q66 13663 Z4 L25 Q67 13664 Z4 L25 Q68 13665 Z4 L25 Q69 13666 Z4 L25 Q70 13667 Z4 L25 Q71 13668 Z4 L25 Q72 13669 Z4 L25 Q73 13670 Z4 L25 Q74 13671 Z4 L25 Q75 13672 Z4 L25 Q76 13673 Z4 L25 Q77 13674 Z4 L25 Q78 13675 Z4 L25 Q79 13676 Z4 L25 Q80 13677 Z4 L25 Q81 13678 Z4 L25 Q82 13679 Z4 L25 Q83 13680 Z4 L25 Q84 13681 Z4 L25 Q85 13682 Z4 L25 Q86 13683 Z4 L25 Q87 13684 Z4 L25 Q88 13685 Z4 L25 Q89 13686 Z4 L25 Q90 13687 Z4 L25 Q91 13688 Z4 L25 Q92 13689 Z4 L25 Q93 13690 Z4 L25 Q94 13691 Z4 L25 Q95 13692 Z4 L25 Q96 13693 Z4 L25 Q97 13694 Z4 L25 Q98 13695 Z4 L25 Q99 13696 Z4 L25 Q100 13697 Z4 L25 Q101 13698 Z4 L25 Q102 13699 Z4 L25 Q103 13700 Z4 L26 Q1 13701 Z4 L26 Q2 13702 Z4 L26 Q3 13703 Z4 L26 Q4 13704 Z4 L26 Q5 13705 Z4 L26 Q6 13706 Z4 L26 Q7 13707 Z4 L26 Q8 13708 Z4 L26 Q9 13709 Z4 L26 Q10 13710 Z4 L26 Q11 13711 Z4 L26 Q12 13712 Z4 L26 Q13 13713 Z4 L26 Q14 13714 Z4 L26 Q15 13715 Z4 L26 Q16 13716 Z4 L26 Q17 13717 Z4 L26 Q18 13718 Z4 L26 Q19 13719 Z4 L26 Q20 13720 Z4 L26 Q21 13721 Z4 L26 Q22 13722 Z4 L26 Q23 13723 Z4 L26 Q24 13724 Z4 L26 Q25 13725 Z4 L26 Q26 13726 Z4 L26 Q27 13727 Z4 L26 Q28 13728 Z4 L26 Q29 13729 Z4 L26 Q30 13730 Z4 L26 Q31 13731 Z4 L26 Q32 13732 Z4 L26 Q33 13733 Z4 L26 Q34 13734 Z4 L26 Q35 13735 Z4 L26 Q36 13736 Z4 L26 Q37 13737 Z4 L26 Q38 13738 Z4 L26 Q39 13739 Z4 L26 Q40 13740 Z4 L26 Q41 13741 Z4 L26 Q42 13742 Z4 L26 Q43 13743 Z4 L26 Q44 13744 Z4 L26 Q45 13745 Z4 L26 Q46 13746 Z4 L26 Q47 13747 Z4 L26 Q48 13748 Z4 L26 Q49 13749 Z4 L26 Q50 13750 Z4 L26 Q51 13751 Z4 L26 Q52 13752 Z4 L26 Q53 13753 Z4 L26 Q54 13754 Z4 L26 Q55 13755 Z4 L26 Q56 13756 Z4 L26 Q57 13757 Z4 L26 Q58 13758 Z4 L26 Q59 13759 Z4 L26 Q60 13760 Z4 L26 Q61 13761 Z4 L26 Q62 13762 Z4 L26 Q63 13763 Z4 L26 Q64 13764 Z4 L26 Q65 13765 Z4 L26 Q66 13766 Z4 L26 Q67 13767 Z4 L26 Q68 13768 Z4 L26 Q69 13769 Z4 L26 Q70 13770 Z4 L26 Q71 13771 Z4 L26 Q72 13772 Z4 L26 Q73 13773 Z4 L26 Q74 13774 Z4 L26 Q75 13775 Z4 L26 Q76 13776 Z4 L26 Q77 13777 Z4 L26 Q78 13778 Z4 L26 Q79 13779 Z4 L26 Q80 13780 Z4 L26 Q81 13781 Z4 L26 Q82 13782 Z4 L26 Q83 13783 Z4 L26 Q84 13784 Z4 L26 Q85 13785 Z4 L26 Q86 13786 Z4 L26 Q87 13787 Z4 L26 Q88 13788 Z4 L26 Q89 13789 Z4 L26 Q90 13790 Z4 L26 Q91 13791 Z4 L26 Q92 13792 Z4 L26 Q93 13793 Z4 L26 Q94 13794 Z4 L26 Q95 13795 Z4 L26 Q96 13796 Z4 L26 Q97 13797 Z4 L26 Q98 13798 Z4 L26 Q99 13799 Z4 L26 Q100 13800 Z4 L26 Q101 13801 Z4 L26 Q102 13802 Z4 L26 Q103 13803 Z4 L27 Q1 13804 Z4 L27 Q2 13805 Z4 L27 Q3 13806 Z4 L27 Q4 13807 Z4 L27 Q5 13808 Z4 L27 Q6 13809 Z4 L27 Q7 13810 Z4 L27 Q8 13811 Z4 L27 Q9 13812 Z4 L27 Q10 13813 Z4 L27 Q11 13814 Z4 L27 Q12 13815 Z4 L27 Q13 13816 Z4 L27 Q14

TABLE 1-75 13842 Z4 L27 Q40 13843 Z4 L27 Q41 13844 Z4 L27 Q42 13845 Z4 L27 Q43 13846 Z4 L27 Q44 13847 Z4 L27 Q45 13848 Z4 L27 Q46 13849 Z4 L27 Q47 13850 Z4 L27 Q48 13851 Z4 L27 Q49 13852 Z4 L27 Q50 13853 Z4 L27 Q51 13854 Z4 L27 Q52 13855 Z4 L27 Q53 13856 Z4 L27 Q54 13857 Z4 L27 Q55 13858 Z4 L27 Q56 13859 Z4 L27 Q57 13860 Z4 L27 Q58 13861 Z4 L27 Q59 13862 Z4 L27 Q60 13863 Z4 L27 Q61 13864 Z4 L27 Q62 13865 Z4 L27 Q63 13866 Z4 L27 Q64 13867 Z4 L27 Q65 13868 Z4 L27 Q66 13869 Z4 L27 Q67 13870 Z4 L27 Q68 13871 Z4 L27 Q69 13872 Z4 L27 Q70 13873 Z4 L27 Q71 13974 Z4 L27 Q72 13875 Z4 L27 Q73 13876 Z4 L27 Q74 13877 Z4 L27 Q75 13878 Z4 L27 Q76 13879 Z4 L27 Q77 13880 Z4 L27 Q78 13881 Z4 L27 Q79 13882 Z4 L27 Q80 13883 Z4 L27 Q81 13884 Z4 L27 Q82 13885 Z4 L27 Q83 13886 Z4 L27 Q84 13887 Z4 L27 Q85 13888 Z4 L27 Q86 13889 Z4 L27 Q87 13890 Z4 L27 Q88 13891 Z4 L27 Q89 13892 Z4 L27 Q90 13893 Z4 L27 Q91 13894 Z4 L27 Q92 13895 Z4 L27 Q93 13896 Z4 L27 Q94 13897 Z4 L27 Q95 13898 Z4 L27 Q96 13899 Z4 L27 Q97 13900 Z4 L27 Q98 13901 Z4 L27 Q99 13902 Z4 L27 Q100 13903 Z4 L27 Q101 13904 Z4 L27 Q102 13905 Z4 L27 Q103 13906 Z4 L28 Q1 13907 Z4 L28 Q2 13908 Z4 L28 Q3 13909 Z4 L28 Q4 13910 Z4 L28 Q5 13911 Z4 L28 Q6 13912 Z4 L28 Q7 13913 Z4 L28 Q8 13914 Z4 L28 Q9 13915 Z4 L28 Q10 13916 Z4 L28 Q11 13917 Z4 L28 Q12 13918 Z4 L28 Q13 13919 Z4 L28 Q14 13920 Z4 L28 Q15 13921 Z4 L28 Q16 13922 Z4 L28 Q17 13923 Z4 L28 Q18 13924 Z4 L23 Q19 13925 Z4 L28 Q20 13926 Z4 L28 Q21 13927 Z4 L28 Q22 13928 Z4 L28 Q23 13929 Z4 L28 Q24 13930 Z4 L28 Q25 13931 Z4 L28 Q26 13932 Z4 L28 Q27 13933 Z4 L28 Q28 13934 Z4 L28 Q29 13935 Z4 L28 Q30 13936 Z4 L28 Q31 13937 Z4 L28 Q32 13938 Z4 L23 Q33 13939 Z4 L28 Q34 13940 Z4 L28 Q35 13941 Z4 L28 Q36 13942 Z4 L28 Q37 13943 Z4 L28 Q38 13944 Z4 L28 Q39 13945 Z4 L28 Q40 13946 Z4 L28 Q41 13947 Z4 L28 Q42 13948 Z4 L28 Q43 13949 Z4 L28 Q44 13950 Z4 L28 Q45 13951 Z4 L28 Q46 13952 Z4 L28 Q47 13953 Z4 L28 Q48 13954 Z4 L28 Q49 13955 Z4 L28 Q50 13956 Z4 L28 Q51 13957 Z4 L28 Q52 13958 Z4 L28 Q53 13959 Z4 L28 Q54 13960 Z4 L28 Q55 13961 Z4 L28 Q56 13962 Z4 L28 Q57 13963 Z4 L28 Q58 13964 Z4 L28 Q59 13965 Z4 L28 Q60 13966 Z4 L28 Q61 13967 Z4 L28 Q62 13968 Z4 L28 Q63 13969 Z4 L28 Q64 13970 Z4 L28 Q65 13971 Z4 L28 Q66 13972 Z4 L28 Q67 13973 Z4 L28 Q68 13974 Z4 L28 Q69 13975 Z4 L28 Q70 13976 Z4 L28 Q71 13977 Z4 L28 Q72 13978 Z4 L28 Q73 13979 Z4 L28 Q74 13980 Z4 L28 Q75 13981 Z4 L28 Q76 13982 Z4 L28 Q77 13983 Z4 L28 Q78 13984 Z4 L28 Q79 13985 Z4 L28 Q80 13986 Z4 L28 Q81 13987 Z4 L28 Q82 13988 Z4 L28 Q83 13989 Z4 L28 Q84 13990 Z4 L28 Q85 13991 Z4 L28 Q86 13992 Z4 L28 Q87 13993 Z4 L28 Q88 13994 Z4 L28 Q89 13995 Z4 L28 Q90 13996 Z4 L28 Q91 13997 Z4 L28 Q92 13998 Z4 L28 Q93 13999 Z4 L28 Q94 14000 Z4 L28 Q95 14001 Z4 L28 Q96 14002 Z4 L28 Q97 14003 Z4 L28 Q98 14004 Z4 L28 Q99 14005 Z4 L28 Q100 14006 Z4 L28 Q101 14007 Z4 L28 Q102 14008 Z4 L28 Q103 14009 Z4 L29 Q1 14010 Z4 L29 Q2 14011 Z4 L29 Q3 14012 Z4 L29 Q4 14013 Z4 L29 Q5 14014 Z4 L29 Q6 14015 Z4 L29 Q7 14016 Z4 L29 Q8 14017 Z4 L29 Q9 14018 Z4 L29 Q10 14019 Z4 L29 Q11 14020 Z4 L29 Q12 14021 Z4 L29 Q13 14022 Z4 L29 Q14 14023 Z4 L29 Q15 14024 Z4 L29 Q16 14025 Z4 L29 Q17 14026 Z4 L29 Q18 14027 Z4 L29 Q19 14028 Z4 L29 Q20 14029 Z4 L29 Q21 14030 Z4 L29 Q22 14031 Z4 L29 Q23 14032 Z4 L29 Q24 14033 Z4 L29 Q25 14034 Z4 L29 Q26 14035 Z4 L29 Q27 14036 Z4 L29 Q28 14037 Z4 L29 Q29 14038 Z4 L29 Q30 14039 Z4 L29 Q31 14040 Z4 L29 Q32 14041 Z4 L29 Q33 14042 Z4 L29 Q34

TABLE 1-76 14043 Z4 L29 Q35 14044 Z4 L29 Q36 14045 Z4 L29 Q37 14046 Z4 L29 Q38 14047 Z4 L29 Q39 14048 Z4 L29 Q40 14049 Z4 L29 Q41 14050 Z4 L29 Q42 14051 Z4 L29 Q43 14052 Z4 L29 Q44 14053 Z4 L29 Q45 14054 Z4 L29 Q46 14055 Z4 L29 Q47 14056 Z4 L29 Q48 14057 Z4 L29 Q49 14058 Z4 L29 Q50 14059 Z4 L29 Q51 14060 Z4 L29 Q52 14061 Z4 L29 Q53 14062 Z4 L29 Q54 14063 Z4 L29 Q55 14064 Z4 L29 Q56 14065 Z4 L29 Q57 14066 Z4 L29 Q58 14067 Z4 L29 Q59 14068 Z4 L29 Q60 14069 Z4 L29 Q61 14070 Z4 L29 Q62 14071 Z4 L29 Q63 14072 Z4 L29 Q64 14073 Z4 L29 Q65 14074 Z4 L29 Q66 14075 Z4 L29 Q67 14076 Z4 L29 Q68 14077 Z4 L29 Q69 14078 Z4 L29 Q70 14079 Z4 L29 Q71 14080 Z4 L29 Q72 14081 Z4 L29 Q73 14082 Z4 L29 Q74 14083 Z4 L29 Q75 14084 Z4 L29 Q76 14085 Z4 L29 Q77 14086 Z4 L29 Q78 14087 Z4 L29 Q79 14088 Z4 L29 Q80 14089 Z4 L29 Q81 14090 Z4 L29 Q82 14091 Z4 L29 Q83 14092 Z4 L29 Q84 14093 Z4 L29 Q85 14094 Z4 L29 Q86 14095 Z4 L29 Q87 14096 Z4 L29 Q88 14097 Z4 L29 Q89 14098 Z4 L29 Q90 14099 Z4 L29 Q91 14100 Z4 L29 Q92 14101 Z4 L29 Q93 14102 Z4 L29 Q94 14103 Z4 L29 Q95 14104 Z4 L29 Q96 14105 Z4 L29 Q97 14106 Z4 L29 Q98 14107 Z4 L29 Q99 14108 Z4 L29 Q100 14109 Z4 L29 Q101 14110 Z4 L29 Q102 14111 Z4 L29 Q103 14112 Z4 L30 Q1 14113 Z4 L30 Q2 14114 Z4 L30 Q3 14115 Z4 L30 Q4 14116 Z4 L30 Q5 14117 Z4 L30 Q6 14118 Z4 L30 Q7 14119 Z4 L30 Q8 14120 Z4 L30 Q9 14121 Z4 L30 Q10 14122 Z4 L30 Q11 14123 Z4 L30 Q12 14124 Z4 L30 Q13 14125 Z4 L30 Q14 14126 Z4 L30 Q15 14127 Z4 L30 Q16 14128 Z4 L30 Q17 14129 Z4 L30 Q18 14130 Z4 L30 Q19 14131 Z4 L30 Q20 14132 Z4 L30 Q21 14133 Z4 L30 Q22 14134 Z4 L30 Q23 14135 Z4 L30 Q24 14136 Z4 L30 Q25 14137 Z4 L30 Q26 14138 Z4 L30 Q27 14139 Z4 L30 Q28 14140 Z4 L30 Q29 14141 Z4 L30 Q30 14142 Z4 L30 Q31 14143 Z4 L30 Q32 14144 Z4 L30 Q33 14145 Z4 L30 Q34 14146 Z4 L30 Q35 14147 Z4 L30 Q36 14148 Z4 L30 Q37 14149 Z4 L30 Q38 14150 Z4 L30 Q39 14151 Z4 L30 Q40 14152 Z4 L30 Q41 14153 Z4 L30 Q42 14154 Z4 L30 Q43 14155 Z4 L30 Q44 14156 Z4 L30 Q45 14157 Z4 L30 Q46 14158 Z4 L30 Q47 14159 Z4 L30 Q48 14160 Z4 L30 Q49 14161 Z4 L30 Q50 14162 Z4 L30 Q51 14163 Z4 L30 Q52 14164 Z4 L30 Q53 14165 Z4 L30 Q54 14166 Z4 L30 Q55 14167 Z4 L30 Q56 14168 Z4 L30 Q57 14169 Z4 L30 Q58 14170 Z4 L30 Q59 14171 Z4 L30 Q60 14172 Z4 L30 Q61 14173 Z4 L30 Q62 14174 Z4 L30 Q63 14175 Z4 L30 Q64 14176 Z4 L30 Q65 14177 Z4 L30 Q66 14178 Z4 L30 Q67 14179 Z4 L30 Q68 14180 Z4 L30 Q69 14181 Z4 L30 Q70 14182 Z4 L30 Q71 14183 Z4 L30 Q72 14184 Z4 L30 Q73 14185 Z4 L30 Q74 14186 Z4 L30 Q75 14187 Z4 L30 Q76 14188 Z4 L30 Q77 14189 Z4 L30 Q78 14190 Z4 L30 Q79 14191 Z4 L30 Q80 14192 Z4 L30 Q81 14193 Z4 L30 Q82 14194 Z4 L30 Q83 14195 Z4 L30 Q84 14196 Z4 L30 Q85 14197 Z4 L30 Q86 14198 Z4 L30 Q87 14199 Z4 L30 Q88 14200 Z4 L30 Q89 14201 Z4 L30 Q90 14202 Z4 L30 Q91 14203 Z4 L30 Q92 14204 Z4 L30 Q93 14205 Z4 L30 Q94 14206 Z4 L30 Q95 14207 Z4 L30 Q96 14208 Z4 L30 Q97 14209 Z4 L30 Q98 14210 Z4 L30 Q99 14211 Z4 L30 Q100 14212 Z4 L30 Q101 14213 Z4 L30 Q102 14214 Z4 L30 Q103 14215 Z4 L31 Q1 14216 Z4 L31 Q2 14217 Z4 L31 Q3 14218 Z4 L31 Q4 14219 Z4 L31 Q5 14220 Z4 L31 Q6 14221 Z4 L31 Q7 14222 Z4 L31 Q8 14223 Z4 L31 Q9 14224 Z4 L31 Q10 14225 Z4 L31 Q11 14226 Z4 L31 Q12 14227 Z4 L31 Q13 14228 Z4 L31 Q14 14229 Z4 L31 Q15 14230 Z4 L31 Q16 14231 Z4 L31 Q17 14232 Z4 L31 Q18 14233 Z4 L31 Q19 14234 Z4 L31 Q20 14235 Z4 L31 Q21 14236 Z4 L31 Q22 14237 Z4 L31 Q23 14238 Z4 L31 Q24 14239 Z4 L31 Q25 14240 Z4 L31 Q26 14241 Z4 L31 Q27 14242 Z4 L31 Q28 14243 Z4 L31 Q29

TABLE 1-77 14244 Z4 L31 Q30 14245 Z4 L31 Q31 14246 Z4 L31 Q32 14247 Z4 L31 Q33 14248 Z4 L31 Q34 14249 Z4 L31 Q35 14250 Z4 L31 Q36 14251 Z4 L31 Q37 14252 Z4 L31 Q38 14253 Z4 L31 Q39 14254 Z4 L31 Q40 14255 Z4 L31 Q41 14256 Z4 L31 Q42 14257 Z4 L31 Q43 14258 Z4 L31 Q44 14259 Z4 L31 Q45 14260 Z4 L31 Q46 14261 Z4 L31 Q47 14262 Z4 L31 Q48 14263 Z4 L31 Q49 14264 Z4 L31 Q50 14265 Z4 L31 Q51 14266 Z4 L31 Q52 14267 Z4 L31 Q53 14268 Z4 L31 Q54 14269 Z4 L31 Q55 14270 Z4 L31 Q56 14271 Z4 L31 Q57 14272 Z4 L31 Q58 14273 Z4 L31 Q59 14274 Z4 L31 Q60 14275 Z4 L31 Q61 14276 Z4 L31 Q62 14277 Z4 L31 Q63 14278 Z4 L31 Q64 14279 Z4 L31 Q65 14280 Z4 L31 Q66 14281 Z4 L31 Q67 14282 Z4 L31 Q68 14283 Z4 L31 Q69 14284 Z4 L31 Q70 14285 Z4 L31 Q71 14286 Z4 L31 Q72 14287 Z4 L31 Q73 14288 Z4 L31 Q74 14289 Z4 L31 Q75 14290 Z4 L31 Q76 14291 Z4 L31 Q77 14292 Z4 L31 Q78 14293 Z4 L31 Q79 14294 Z4 L31 Q80 14295 Z4 L31 Q81 14296 Z4 L31 Q82 14297 Z4 L31 Q83 14298 Z4 L31 Q84 14299 Z4 L31 Q85 14300 Z4 L31 Q86 14301 Z4 L31 Q87 14302 Z4 L31 Q88 14303 Z4 L31 Q89 14304 Z4 L31 Q90 14305 Z4 L31 Q91 14306 Z4 L31 Q92 14307 Z4 L31 Q93 14308 Z4 L31 Q94 14309 Z4 L31 Q95 14310 Z4 L31 Q96 14311 Z4 L31 Q97 14312 Z4 L31 Q98 14313 Z4 L31 Q99 14314 Z4 L31 Q100 14315 Z4 L31 Q101 14316 Z4 L31 Q102 14317 Z4 L31 Q103 14318 Z4 L32 Q1 14319 Z4 L32 Q2 14320 Z4 L32 Q3 14321 Z4 L32 Q4 14322 Z4 L32 Q5 14323 Z4 L32 Q6 14324 Z4 L32 Q7 14325 Z4 L32 Q8 14326 Z4 L32 Q9 14327 Z4 L32 Q10 14328 Z4 L32 Q11 14329 Z4 L32 Q12 14330 Z4 L32 Q13 14331 Z4 L32 Q14 14332 Z4 L32 Q15 14333 Z4 L32 Q16 14334 Z4 L32 Q17 14335 Z4 L32 Q18 14336 Z4 L32 Q19 14337 Z4 L32 Q20 14338 Z4 L32 Q21 14339 Z4 L32 Q22 14340 Z4 L32 Q23 14341 Z4 L32 Q24 14342 Z4 L32 Q25 14343 Z4 L32 Q26 14344 Z4 L32 Q27 14345 Z4 L32 Q28 14346 Z4 L32 Q29 14347 Z4 L32 Q30 14348 Z4 L32 Q31 14349 Z4 L32 Q32 14350 Z4 L32 Q33 14351 Z4 L32 Q34 14352 Z4 L32 Q35 14353 Z4 L32 Q36 14354 Z4 L32 Q37 14355 Z4 L32 Q38 14356 Z4 L32 Q39 14357 Z4 L32 Q40 14358 Z4 L32 Q41 14359 Z4 L32 Q42 14360 Z4 L32 Q43 14361 Z4 L32 Q44 14362 Z4 L32 Q45 14363 Z4 L32 Q46 14364 Z4 L32 Q47 14365 Z4 L32 Q48 14366 Z4 L32 Q49 14367 Z4 L32 Q50 14368 Z4 L32 Q51 14369 Z4 L32 Q52 14370 Z4 L32 Q53 14371 Z4 L32 Q54 14372 Z4 L32 Q55 14373 Z4 L32 Q56 14374 Z4 L32 Q57 14375 Z4 L32 Q58 14376 Z4 L32 Q59 14377 Z4 L32 Q60 14378 Z4 L32 Q61 14379 Z4 L32 Q62 14380 Z4 L32 Q63 14381 Z4 L32 Q64 14382 Z4 L32 Q65 14383 Z4 L32 Q66 14384 Z4 L32 Q67 14385 Z4 L32 Q68 14386 Z4 L32 Q69 14387 Z4 L32 Q70 14388 Z4 L32 Q71 14389 Z4 L32 Q72 14390 Z4 L32 Q73 14391 Z4 L32 Q74 14392 Z4 L32 Q75 14393 Z4 L32 Q76 14394 Z4 L32 Q77 14395 Z4 L32 Q78 14396 Z4 L32 Q79 14397 Z4 L32 Q80 14398 Z4 L32 Q81 14399 Z4 L32 Q82 14400 Z4 L32 Q83 14401 Z4 L32 Q84 14402 Z4 L32 Q85 14403 Z4 L32 Q86 14404 Z4 L32 Q87 14405 Z4 L32 Q88 14406 Z4 L32 Q89 14407 Z4 L32 Q90 14408 Z4 L32 Q91 14409 Z4 L32 Q92 14410 Z4 L32 Q93 14411 Z4 L32 Q94 14412 Z4 L32 Q95 14413 Z4 L32 Q96 14414 Z4 L32 Q97 14415 Z4 L32 Q98 14416 Z4 L32 Q99 14417 Z4 L32 Q100 14418 Z4 L32 Q101 14419 Z4 L32 Q102 14420 Z4 L32 Q103 14421 Z4 L33 Q1 14422 Z4 L33 Q2 14423 Z4 L33 Q3 14424 Z4 L33 Q4 14425 Z4 L33 Q5 14426 Z4 L33 Q6 14427 Z4 L33 Q7 14428 Z4 L33 Q8 14429 Z4 L33 Q9 14430 Z4 L33 Q10 14431 Z4 L33 Q11 14432 Z4 L33 Q12 14433 Z4 L33 Q13 14434 Z4 L33 Q14 14435 Z4 L33 Q15 14436 Z4 L33 Q16 14437 Z4 L33 Q17 14438 Z4 L33 Q18 14439 Z4 L33 Q19 14440 Z4 L33 Q20 14441 Z4 L33 Q21 14442 Z4 L33 Q22 14443 Z4 L33 Q23 14444 Z4 L33 Q24

TABLE 1-78 14445 Z4 L33 Q25 14446 Z4 L33 Q26 14447 Z4 L33 Q27 14448 Z4 L33 Q28 14449 Z4 L33 Q29 14450 Z4 L33 Q30 14451 Z4 L33 Q31 14452 Z4 L33 Q32 14453 Z4 L33 Q33 14454 Z4 L33 Q34 14455 Z4 L33 Q35 14456 Z4 L33 Q36 14457 Z4 L33 Q37 14458 Z4 L33 Q38 14459 Z4 L33 Q39 14460 Z4 L33 Q40 14461 Z4 L33 Q41 14462 Z4 L33 Q42 14463 Z4 L33 Q43 14464 Z4 L33 Q44 14465 Z4 L33 Q45 14466 Z4 L33 Q46 14467 Z4 L33 Q47 14468 Z4 L33 Q48 14469 Z4 L33 Q49 14470 Z4 L33 Q50 14471 Z4 L33 Q51 14472 Z4 L33 Q52 14473 Z4 L33 Q53 14474 Z4 L33 Q54 14475 Z4 L33 Q55 14476 Z4 L33 Q56 14477 Z4 L33 Q57 14478 Z4 L33 Q58 14479 Z4 L33 Q59 14480 Z4 L33 Q60 14481 Z4 L33 Q61 14482 Z4 L33 Q62 14483 Z4 L33 Q63 14484 Z4 L33 Q64 14485 Z4 L33 Q65 14486 Z4 L33 Q66 14487 Z4 L33 Q67 14488 Z4 L33 Q68 14489 Z4 L33 Q69 14490 Z4 L33 Q70 14491 Z4 L33 Q71 14492 Z4 L33 Q72 14493 Z4 L33 Q73 14494 Z4 L33 Q74 14495 Z4 L33 Q75 14496 Z4 L33 Q76 14497 Z4 L33 Q77 14498 Z4 L33 Q78 14499 Z4 L33 Q79 14500 Z4 L33 Q80 14501 Z4 L33 Q81 14502 Z4 L33 Q82 14503 Z4 L33 Q83 14504 Z4 L33 Q84 14505 Z4 L33 Q85 14506 Z4 L33 Q86 14507 Z4 L33 Q87 14508 Z4 L33 Q88 14509 Z4 L33 Q89 14510 Z4 L33 Q90 14511 Z4 L33 Q91 14512 Z4 L33 Q92 14513 Z4 L33 Q93 14514 Z4 L33 Q94 14515 Z4 L33 Q95 14516 Z4 L33 Q96 14517 Z4 L33 Q97 14518 Z4 L33 Q98 14519 Z4 L33 Q99 14520 Z4 L33 Q100 14521 Z4 L33 Q101 14522 Z4 L33 Q102 14523 Z4 L33 Q103 14524 Z4 L34 Q1 14525 Z4 L34 Q2 14526 Z4 L34 Q3 14527 Z4 L34 Q4 14528 Z4 L34 Q5 14529 Z4 L34 Q6 14530 Z4 L34 Q7 14531 Z4 L34 Q8 14532 Z4 L34 Q9 14533 Z4 L34 Q10 14534 Z4 L34 Q11 14535 Z4 L34 Q12 14536 Z4 L34 Q13 14537 Z4 L34 Q14 14538 Z4 L34 Q15 14539 Z4 L34 Q16 14540 Z4 L34 Q17 14541 Z4 L34 Q18 14542 Z4 L34 Q19 14543 Z4 L34 Q20 14544 Z4 L34 Q21 14545 Z4 L34 Q22 14546 Z4 L34 Q23 14547 Z4 L34 Q24 14548 Z4 L34 Q25 14549 Z4 L34 Q26 14550 Z4 L34 Q27 14551 Z4 L34 Q28 14552 Z4 L34 Q29 14553 Z4 L34 Q30 14554 Z4 L34 Q31 14555 Z4 L34 Q32 14556 Z4 L34 Q33 14557 Z4 L34 Q34 14558 Z4 L34 Q35 14559 Z4 L34 Q36 14560 Z4 L34 Q37 14561 Z4 L34 Q38 14562 Z4 L34 Q39 14563 Z4 L34 Q40 14564 Z4 L34 Q41 14565 Z4 L34 Q42 14566 Z4 L34 Q43 14567 Z4 L34 Q44 14568 Z4 L34 Q45 14569 Z4 L34 Q46 14570 Z4 L34 Q47 14571 Z4 L34 Q48 14572 Z4 L34 Q49 14573 Z4 L34 Q50 14574 Z4 L34 Q51 14575 Z4 L34 Q52 14576 Z4 L34 Q53 14577 Z4 L34 Q54 14578 Z4 L34 Q55 14579 Z4 L34 Q56 14580 Z4 L34 Q57 14581 Z4 L34 Q58 14582 Z4 L34 Q59 14583 Z4 L34 Q60 14584 Z4 L34 Q61 14585 Z4 L34 Q62 14586 Z4 L34 Q63 14587 Z4 L34 Q64 14588 Z4 L34 Q65 14589 Z4 L34 Q66 14590 Z4 L34 Q67 14591 Z4 L34 Q68 14592 Z4 L34 Q69 14593 Z4 L34 Q70 14594 Z4 L34 Q71 14595 Z4 L34 Q72 14596 Z4 L34 Q73 14597 Z4 L34 Q74 14598 Z4 L34 Q75 14599 Z4 L34 Q76 14600 Z4 L34 Q77 14601 Z4 L34 Q78 14602 Z4 L34 Q79 14603 Z4 L34 Q80 14604 Z4 L34 Q81 14605 Z4 L34 Q82 14606 Z4 L34 Q63 14607 Z4 L34 Q84 14608 Z4 L34 Q85 14609 Z4 L34 Q86 14610 Z4 L34 Q87 14611 Z4 L34 Q88 14612 Z4 L34 Q89 14613 Z4 L34 Q90 14614 Z4 L34 Q91 14615 Z4 L34 Q92 14616 Z4 L34 Q93 14617 Z4 L34 Q94 14618 Z4 L34 Q95 14619 Z4 L34 Q96 14620 Z4 L34 Q97 14621 Z4 L34 Q98 14622 Z4 L34 Q99 14623 Z4 L34 Q100 14624 Z4 L34 Q101 14625 Z4 L34 Q102 14626 Z4 L34 Q103 14627 Z4 L35 Q1 14628 Z4 L35 Q2 14629 Z4 L35 Q3 14630 Z4 L35 Q4 14631 Z4 L35 Q5 14632 Z4 L35 Q6 14633 Z4 L35 Q7 14634 Z4 L35 Q8 14635 Z4 L35 Q9 14636 Z4 L35 Q10 14637 Z4 L35 Q11 14638 Z4 L35 Q12 14639 Z4 L35 Q13 14640 Z4 L35 Q14 14641 Z4 L35 Q15 14642 Z4 L35 Q16 14643 Z4 L35 Q17 14644 Z4 L35 Q18 14645 Z4 L35 Q19

TABLE 1-79 14646 Z4 L35 Q20 14647 Z4 L35 Q21 14648 Z4 L35 Q22 14649 Z4 L35 Q23 14650 Z4 L35 Q24 14651 Z4 L35 Q25 14652 Z4 L35 Q26 14653 Z4 L35 Q27 14654 Z4 L35 Q28 14655 Z4 L35 Q29 14656 Z4 L35 Q30 14657 Z4 L35 Q31 14658 Z4 L35 Q32 14659 Z4 L35 Q33 14660 Z4 L35 Q34 14661 Z4 L35 Q35 14662 Z4 L35 Q36 14663 Z4 L35 Q37 14664 Z4 L35 Q38 14665 Z4 L35 Q39 14666 Z4 L35 Q40 14667 Z4 L35 Q41 14668 Z4 L35 Q42 14669 Z4 L35 Q43 14670 Z4 L35 Q44 14671 Z4 L35 Q45 14672 Z4 L35 Q46 14673 Z4 L35 Q47 14674 Z4 L35 Q48 14675 Z4 L35 Q49 14676 Z4 L35 Q50 14677 Z4 L35 Q51 14678 Z4 L35 Q52 14679 Z4 L35 Q53 14680 Z4 L35 Q54 14681 Z4 L35 Q55 14682 Z4 L35 Q56 14683 Z4 L35 Q57 14684 Z4 L35 Q58 14685 Z4 L35 Q59 14686 Z4 L35 Q60 14687 Z4 L35 Q61 14688 Z4 L35 Q62 14689 Z4 L35 Q63 14690 Z4 L35 Q64 14691 Z4 L35 Q65 14692 Z4 L35 Q66 14693 Z4 L35 Q67 14694 Z4 L35 Q68 14695 Z4 L35 Q69 14696 Z4 L35 Q70 14697 Z4 L35 Q71 14698 Z4 L35 Q72 14699 Z4 L35 Q73 14700 Z4 L35 Q74 14701 Z4 L35 Q75 14702 Z4 L35 Q76 14703 Z4 L35 Q77 14704 Z4 L35 Q78 14705 Z4 L35 Q79 14706 Z4 L35 Q80 14707 Z4 L35 Q81 14708 Z4 L35 Q82 14709 Z4 L35 Q83 14710 Z4 L35 Q84 14711 Z4 L35 Q85 14712 Z4 L35 Q86 14713 Z4 L35 Q87 14714 Z4 L35 Q88 14715 Z4 L35 Q89 14716 Z4 L35 Q90 14717 Z4 L35 Q91 14718 Z4 L35 Q92 14719 Z4 L35 Q93 14720 Z4 L35 Q94 14721 Z4 L35 Q95 14722 Z4 L35 Q96 14723 Z4 L35 Q97 14724 Z4 L35 Q98 14725 Z4 L35 Q99 14726 Z4 L35 Q100 14727 Z4 L35 Q101 14728 Z4 L35 Q102 14729 Z4 L35 Q103 14730 Z4 L36 Q1 14731 Z4 L36 Q2 14732 Z4 L36 Q3 14733 Z4 L36 Q4 14734 Z4 L36 Q5 14735 Z4 L36 Q6 14736 Z4 L36 Q7 14737 Z4 L36 Q8 14738 Z4 L36 Q9 14739 Z4 L36 Q10 14740 Z4 L36 Q11 14741 Z4 L36 Q12 14742 Z4 L36 Q13 14743 Z4 L36 Q14 14744 Z4 L36 Q15 14745 Z4 L36 Q16 14746 Z4 L36 Q17 14747 Z4 L36 Q18 14748 Z4 L36 Q19 14749 Z4 L36 Q20 14750 Z4 L36 Q21 14751 Z4 L36 Q22 14752 Z4 L36 Q23 14753 Z4 L36 Q24 14754 Z4 L36 Q25 14755 Z4 L36 Q26 14756 Z4 L36 Q27 14757 Z4 L36 Q28 14758 Z4 L36 Q29 14759 Z4 L36 Q30 14760 Z4 L36 Q31 14761 Z4 L36 Q32 14762 Z4 L36 Q33 14763 Z4 L36 Q34 14764 Z4 L36 Q35 14765 Z4 L36 Q36 14766 Z4 L36 Q37 14767 Z4 L36 Q38 14768 Z4 L36 Q39 14769 Z4 L36 Q40 14770 Z4 L36 Q41 14771 Z4 L36 Q42 14772 Z4 L36 Q43 14773 Z4 L36 Q44 14774 Z4 L36 Q45 14775 Z4 L36 Q46 14776 Z4 L36 Q47 14777 Z4 L36 Q48 14778 Z4 L36 Q49 14779 Z4 L36 Q50 14780 Z4 L36 Q51 14781 Z4 L36 Q52 14782 Z4 L36 Q53 14783 Z4 L36 Q54 14784 Z4 L36 Q55 14785 Z4 L36 Q56 14786 Z4 L36 Q57 14787 Z4 L36 Q58 14788 Z4 L36 Q59 14789 Z4 L36 Q60 14790 Z4 L36 Q61 14791 Z4 L36 Q62 14792 Z4 L36 Q63 14793 Z4 L36 Q64 14794 Z4 L36 Q65 14795 Z4 L36 Q66 14796 Z4 L36 Q67 14797 Z4 L36 Q68 14798 Z4 L36 Q69 14799 Z4 L36 Q70 14800 Z4 L36 Q71 14801 Z4 L36 Q72 14802 Z4 L36 Q73 14803 Z4 L36 Q74 14804 Z4 L36 Q75 14805 Z4 L36 Q76 14806 Z4 L36 Q77 14807 Z4 L36 Q78 14808 Z4 L36 Q79 14809 Z4 L36 Q80 14810 Z4 L36 Q81 14811 Z4 L36 Q82 14812 Z4 L36 Q83 14813 Z4 L36 Q84 14814 Z4 L36 Q85 14815 Z4 L36 Q86 14816 Z4 L36 Q87 14817 Z4 L36 Q88 14818 Z4 L36 Q89 14819 Z4 L36 Q90 14820 Z4 L36 Q91 14821 Z4 L36 Q92 14822 Z4 L36 Q93 14823 Z4 L36 Q94 14824 Z4 L36 Q95 14825 Z4 L36 Q96 14826 Z4 L36 Q97 14827 Z4 L36 Q98 14828 Z4 L36 Q99 14829 Z4 L36 Q100 14830 Z4 L36 Q101 14831 Z4 L36 Q102 14832 Z4 L36 Q103

A specific example of another embodiment of the compound of the invention includes a compound represented by formula (11)

or a pharmaceutically acceptable salt thereof, wherein Z, L¹, L², X, R¹, R², R³, and R⁴ are the same as the definitions herein, R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), and R^(a1) is the same as the definition herein.

A specific example of another embodiment of the compound of the invention includes a compound represented by formula (12)

or a pharmaceutically acceptable salt thereof, wherein X, R¹, R², R³, and R⁴ are the same as the definitions herein, R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), and R^(a1) is the same as the definition herein. A compound of formula (12) is in an interchangeable relationship with, and thus can be biologically equivalent with, a compound of formula (1a) or (3a) due to an equilibrium reaction in an aqueous solution or in the body.

A specific example of another embodiment of the compound of the invention includes a compound represented by formula (13)

or a pharmaceutically acceptable salt thereof, wherein X, Y, ring A, L³, L⁴, R¹, R², R⁴, and R⁵ are the same as the definitions herein, R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), and R^(a1) is the same as the definition herein.

A specific example of a preferred embodiment of the compound of the invention includes a compound represented by formula (14)

or a pharmaceutically acceptable salt thereof, wherein X, L³, L⁴, m, n, and R⁵ are the same as the definitions herein, R^(G) is a hydroxyl group, a thiol group, or —NHR^(a1), and R^(a1) is the same as the definition herein.

The compound of the invention is described further hereinafter.

The compound of the invention can have, depending on the type of substituent, a tautomer, stereoisomers such as geometric isomer, and enantiomer, which are encompassed by the present invention. Specifically, if the compound of the invention has one or more asymmetric carbon atoms, there is a diastereomer or an enantiomer, where a mixture of such a diastereomer or enantiomer or isolated diastereomer or enantiomer are also encompassed by the compound of the invention.

The compound of the invention can also have a structure represented by the following formula (11) due to an equilibrium state or the like, depending on the environment conditions such as temperature or humidity, or a physical factor in a solid, liquid, solution, or the like. The compound of the invention also encompasses compounds with such a structure.

In formula (11), X represents a hydroxyl group, a thiol group, or —NHR^(a1), Z, L¹, L², R^(G), R¹, R², R³, R⁴, and R^(a1) are defined the same as the definitions herein, and formula (1a) is defined the same as the definition herein.

For example, the structures of the compounds in the Examples herein are based on estimation considered the most appropriate by those skilled in the art using proton nuclear magnetic resonance spectrum (¹H-NMR), liquid chromatography mass spectrometry (LCMS), or the like, but the structures are just estimates under each specific measurement environment. In particular, the structure of formula (1a), the structure of formula (1b), and the structure of formula (11) are possibly converted to each other or partially converted to one of the structures and mixed due to a property unique to each compound, various environmental conditions such as temperature or humidity, or physical factor in a solid, liquid, solution or the like.

The compound of the invention also includes various hydrates, solvates, and crystalline polymorphisms.

Furthermore, the compound of the invention may be substituted with an isotope (e.g., ²H (or D), ³H (or T), ¹¹C, ¹³C, ¹⁴C, ¹³N, ¹⁵N, ¹⁵O, ³⁵S, ¹⁸F, ¹²⁵I, or the like). Such compounds are also encompassed by the compound of the invention.

Prodrugs of the compound of the invention are also within the scope of the invention. As used herein, a prodrug refers to a derivative that results in the compound of formula (1a), (1b), or (11) by acid hydrolysis or enzymatic degradation in the body. If, for example, the compound of formula (1a), (1b), or (11) has a hydroxyl group, amino group, or carboxyl group, these groups can be modified in accordance with a conventional method to manufacture a prodrug.

Examples for a compound with a carboxy group include compounds whose carboxyl group has been converted to an alkoxycarbonyl group, alkylthiocarbonyl group, or alkylaminocarbonyl group.

Examples for a compound with an amino group include compounds whose amino group has been substituted with an alkanoyl group to be converted to an alkanoylamino group, substituted with an alkoxycarbonyl group to be converted to an alkoxycarbonylamino group, modified to an alkanoyloxymethylamino group, or converted to a hydroxylamine.

Examples for a compound with a hydroxyl group include compounds whose hydroxyl group has been substituted with the alkanoyl group described above to be converted to an alkanoyloxy group, converted to a phosphate ester, or converted to an alkanoyloxymethyloxy group.

Examples of the alkyl moiety of a group used in producing these prodrugs include the alkyl group described above. The alkyl group is optionally substituted with, for example, an alkoxy group or the like. Preferred examples thereof include the following.

Examples of compounds whose carboxyl group has been converted to an alkoxycarbonyl group include alkoxycarbonyl such as methoxycarbonyl and ethoxycarbonyl, and alkoxycarbonyl substituted with an alkoxy group such as methoxymethoxycarbonyl, ethoxymethoxycarbonyl, 2-methoxyethoxycarbonyl, 2-methoxyethoxymethoxycarbonyl, and pivaloyloxymethoxycarbonyl.

As used herein, “pharmaceutically acceptable salt” refers to an acid addition salt or base addition salt which is pharmaceutically acceptable for use. Examples of “pharmaceutically acceptable salts” include, but are not limited to, acid addition salts such as acetate, propionate, butyrate, formate, trifluoroacetate, maleate, fumarate, tartrate, citrate, stearate, succinate, ethylsuccinate, malonate, lactobionate, gluconate, glucoheptonate, benzoate, methanesulfonate, benzenesulfonate, para-toluenesulfonate (tosylate), laurylsulfate, malate, ascorbate, mandelate, saccharinate, xinafoate, pamoate, cinnamate, adipate, cysteine salt, N-acetyl cysteine salt, hydrochloride, hydrobromide, phosphate, sulfate, hydroiodide, nicotinate, oxalate, picrate, thiocyanate, undecanoate, acrylic acid polymer salt, and carboxyvinyl polymer; inorganic base addition salts such as lithium salt, sodium salt, potassium salt, and calcium salt; organic base addition salts such as morpholine and piperidine; amino acid addition salts wherein the amino acid is aspartic acid or glutamic acid; and the like.

The compounds of the invention can be administered directly, or as a formulation, medicament, or a pharmaceutical composition using a suitable dosage form, by oral or parenteral administration. Specific examples of such dosage forms include, but are not limited to, tablets, capsules, powder, granules, liquid agents, suspension, injections, patches, poultice, and the like. These formulations can be manufactured by a known method using an additive that is commonly used as a pharmaceutical additive.

As these additives, an excipient, disintegrant, binding agent, fluidizer, lubricant, coating agent, solubilizing agent, solubilization promotor, thickener, dispersant, stabilizer, sweetener, flavoring agent, or the like can be used depending on the objective. Specific examples of these additives include, but are not limited to, lactose, mannitol, crystalline cellulose, low-substituted hydroxypropyl cellulose, corn starch, partially pregelatinized starch, carmellose calcium, croscarmellose sodium, hydroxypropyl cellulose, hydroxypropyl methylcellulose, polyvinyl alcohol, magnesium stearate, sodium stearyl fumarate, polyethylene glycol, propylene glycol, titanium oxide, talc, and the like.

The dosage of the compound of the invention is appropriately selected depending on the animal targeted for administration, route of administration, disease, patient's age, body weight, and symptom. For example, the dosage is 0.01 mg as the lower limit (preferably 100 mg) and 10000 mg as the upper limit (preferably 6000 mg) per day for adults for oral administration. This amount can be administered once daily, or divided into several doses.

The compound of the invention is a compound with inhibitory activity against β-lactamase. Thus, the compound can be a prophylactic or therapeutic agent that is useful for a bacterial infection by combined use with an antimicrobial agent. Specific examples of such bacterial infections include sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, an odontogenic infection, and the like.

The compound of the invention can be used in combination with at least one agent selected from an antimicrobial agent, an antifungal agent, an antiviral agent, an anti-inflammatory agent, or an anti-allergic agent for treating one or more bacterial infections described herein. The agent is preferably an antimicrobial agent, and more preferably a β-lactam agent. Specific examples thereof include amoxicillin, ampicillin (pivampicillin, hetacillin, bacampicillin, metampicillin, and talampicillin), epicillin, carbenicillin (carindacillin), ticarcillin, temocillin, azlocillin, piperacillin, mezlocillin, mecillinam (pivmecillinam), sulbenicillin, benzylpenicillin (G), clometocillin, benzathine benzylpenicillin, procaine benzylpenicillin, azidocillin, penamecillin, phenoxymethyl penicillin (V), propicillin, benzathine phenoxymethylpenicillin, phenethicillin, cloxacillin (dicloxacillin and flucloxacillin), oxacillin, methicillin, nafcillin, faropenem, biapenem, doripenem, ertapenem, imipenem, meropenem, panipenem, tomopenem, razupenem, cefazolin, cefacetrile, cefadroxil, cephalexin, cefaloglycin, cefalonium, cefaloridine, cephalothin, cephapirin, cefatrizine, cefazedone, cefazaflur, cefradine, cefroxadine, ceftezole, cefaclor, cefamandole, cefminox, cefonicide, ceforanide, cefotiam, cefprozil, cefbuperazone, cefuroxime, cefuzonam, cefoxitin, cefotetan, cefmetazole, loracarbef, cefixime, ceftazidime, ceftriaxone, cefcapene, cefdaloxime, cefdinir, cefditoren, cefetamet, cefmenoxime, cefodizime, cefoperazone, cefotaxime, cefpimizole, cefpiramide, cefpodoxime, cefsulodin, cefteram, ceftibuten, ceftiolene, ceftizoxime, flomoxef, latamoxef, cefepime, cefozopran, cefpirome, cefquinome, ceftobiprole, ceftaroline, CXA-101, RWJ-54428, MC-04546, ME1036, BAL30072, SYN2416, ceftiofur, cefquinome, cefovecin, aztreonam, tigemonam, carumonam, RWJ-442831, RWJ-333441, and RWJ-333442. The timing of dosing of the compound of the invention and therapeutic agents thereof is not limited. The compound and therapeutic agent can be administered concurrently or sequentially to a subject being administered therewith. The compound of the invention and the therapeutic agents can be formulated as a combined agent. The dosage of the therapeutic agent can be appropriately selected based on the clinically used dose. The ratio of the compound of the invention and the therapeutic agents can be appropriately selected depending on the subject of administration, route of administration, target disease, symptom, combination, or the like.

In another embodiment, the compound of the invention can be combined and administered concomitantly or administered at different times upon use of a pharmaceutical composition comprising an antimicrobial agent such as a β-lactam agent. Such a pharmaceutical composition comprising a β-lactam agent is also within the scope of the invention, and can be used for treating or preventing a bacterial infection such as sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, a deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, a urinary tract infection, a genital infection, an eye infection, or an odontogenic infection.

Such a medicament, formulation, or pharmaceutical composition can be manufactured by mixing the compound of the invention and/or an addition agent (e.g., antimicrobial agent such as a β-lactam agent) with any suitable component, together or separately, as a combined agent or as separate agents using any technology that is known in the art. An appropriate formulation such as a tablet, capsule, powder, granule, liquid agent, suspension, injection, patch, or poultice can be formulated by using any technology that is known in the art. If the compound of the invention and/or an addition agent (e.g., antimicrobial agent such as a β-lactam agent) are prepared as separate agents, they can be provided as a kit of two agents. The kit can provide one of the components as a single agent, with instructions (package insert or the like) instructing to combine and administer the other component (for the compound of the invention, the additional agent (e.g., antimicrobial agent such as a β-lactam agent); for the addition agent (e.g., antimicrobial agent such as a β-lactam agent), the compound of the invention) concurrently or at different times.

If the compound of the invention is used as an active ingredient of a medicament, the compound can be intended for use in not just humans, but also animals other than humans (cat, dog, cow, chicken, fish, and the like).

Hereinafter, the method of manufacturing the compound of the invention is described with examples, but the present invention is not limited thereto.

The compound of the invention can be manufactured by, for example, the manufacturing methods described below, but the methods are not limited to such methods. These manufacturing methods can be appropriately improved upon based on the expertise of those skilled in the art of organic synthetic chemistry. Salts of the compounds used as a starting material can be used in the manufacturing method described below, as long as the reaction is not affected.

In the manufacturing methods described below, even if use of a protecting group is not specifically described, a functional group other than those at the reaction point can be protected as needed and deprotected after the completion of a reaction or after a series of reactions to obtain a compound of interest if one of the functional groups other than those at the reaction point is altered under the reaction condition or if it is unsuitable for post-reaction processing. Common protecting groups described in the document (T. W. Greene and P. G. M. Wuts, “Protective Group in Organic Synthesis”, 3^(rd) Ed., John Wiley and Sons, Inc., New York (1999)) or the like can be used as the protecting groups used in these processes. A protecting group can be introduced or removed by a method that is commonly used in organic synthetic chemistry (e.g., method described in the aforementioned document or the like) or a method in accordance therewith.

The starting material and intermediate in the manufacturing methods described below can be purchased as a commercially available product or are available by synthesis in accordance with a method described in a known document or a known method from a known compound. Salts of the starting material and intermediate can also be used, as long as the reaction is not affected.

The intermediate and compound of interest in the manufacturing methods described below can also be converted into another compound encompassed by the present invention by appropriately converting their functional groups. A functional group can be converted, in doing so, by a method that is commonly used in organic synthetic chemistry (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) or a method in accordance therewith.

An inert solvent in the manufacturing methods described below refers to a solvent that does not react with starting materials, reagents, bases, acids, catalysts, ligands, or the like used in a reaction (hereinafter, also referred to as “starting materials or the like used in a reaction”). A solvent used in each step can be used as an inert solvent even if the solvent reacts with the starting materials or the like used in the reaction, as long as the reaction of interest proceeds to result in a compound of interest.

Manufacturing Method 1

The compound of formula (1a), which is represented by formula (1-7) can be manufactured, for example, by the following manufacturing method.

wherein L¹, L², Y, Z, ring A, L³, L⁴, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, LG represents a leaving group (e.g., a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesultonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy, or the like), T represents a hydroxyl group or a leaving group (e.g., a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy, or the like), PG¹ represents a protecting group of a hydroxyl group (e.g., a tert-butoxycarbonyl group, acetyl group, methoxymethyl group, p-methoxybenzyl group, tert-butyldimethylsilyl group, trimethylsilyl group, or the like), and PG² and PG³ represent protecting groups of boronic acid (e.g., an optionally substituted C₁₋₆ alkyl group, a structure represented by the following formula, or the like).

PG⁴ represents a hydrogen atom, a protecting group of a hydroxyl group (e.g., a tert-butoxycarbonyl group, acetyl group, methoxymethyl group, p-methoxybenzyl group, tert-butyldimethylsilyl group, trimethylsilyl group, or the like), a protecting group of a thiol group (e.g., an acetamidomethyl group or trityl group), or a protecting group of an amino group (e.g., an ethoxycarbonyl group, tert-butoxycarbonyl group, acetyl group, benzoyl group, trifluoroacetyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, triphenylmethyl group, methanesulfonyl group, p-toluenesulfonyl group, trimethylsilyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, benzylsulfonyl group, benzyl group, 4-nitrobenzyl group, 4-methoxybenzyl group, methyl group, ethyl group, or the like).

A commercially available product or a compound manufactured by a known method (e.g., WO 2016/003929, WO 2016/149393, or the like) can be used as a starting raw material compound (1-1).

A commercially available product that is purchased or a compound synthesized in accordance with a method described in a known document (WO 2016/149393, Journal of Heterocyclic Chemistry, 15(8), 1295, 1978, Journal of Heterocyclic Chemistry, 44(2), 279, 2007, Eur. J. Med. Chem., 64, 54, 2013, J. Med. Chem., 2012, 55, 2945, J. Med. Chem., 2005, 48, 1984, Tetrahedron Letters, 57, 2888, 2016, WO 2012/018668, or the like) or a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (1-2).

A commercially available product that is purchased or a compound synthesized in accordance with a method described in a known document (e.g., WO 2008/008895, WO 2011/118818, J. Med. Chem., 28(11), 1721, 1985, Tetrahedron, 67(52), 10208, 2011, Tetrahedron Letters, 26(39), 4739, 1985, J. Antibiot. 59(4), 241, 2006, or the like) or a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (1-5).

As compound (1-2) and compound (1-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 1-1: Compound (1-3) can be manufactured by reacting compound (1-1) with compound (1-2) in an inert solvent in the presence of a base under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and DME, halogenated hydrocarbon solvents such as dichloromethane or dichloroethane, aprotic solvents such as N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO), and the like. Examples of base include potassium tert-butoxy, sodium hydride, triethylamine, diisopropylethylamine, potassium carbonate, sodium carbonate, and the like. A base can be used at 0.001 to 100 equivalents with respect to compound (1-1), which is preferably 0.5 to 10 equivalents. Compound (1-2) can be used at 0.001 to 100 equivalents with respect to compound (1-1), which is preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −10° C. to about 100° C.

Step 1-2: Compound (1-4) can be manufactured by deprotecting the protecting group PG¹ of compound (1-3). This step can be performed in accordance with the method described in, for example, the document (T. W. Greene and P. G. M. Wuts, “Protective Group in Organic Synthesis”, 3^(rd) Ed., John Wiley and Sons, Inc., New York (1999)) or the like.

Step 1-3: Compound (1-6) can be manufactured using Manufacturing Method (1-3-1) or Manufacturing Method (1-3-2) described below.

Step 1-3-1: If Y is an oxygen atom and T is a hydroxyl group, compound (1-6) can be manufactured by reacting compound (1-4) with compound (1-5) under the so-called Mitsunobu reaction in an inert solvent, in the presence of an azo compound analog and organic phosphorous compound or in the presence of a phosphorane compound under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and DME, hydrocarbon solvents such as toluene and benzene, and the like. Examples of azo compound analog include diethyl azodicarboxylate, diisopropyl azodicarboxylate, and the like. An azo compound analog can be used at 0.001 to 100 molar equivalents with respect to compound (1-4), which is preferably 1 to 10 molar equivalents. Examples of the organic phosphorous compound include triphenylphosphine, tributylphosphine, and the like. An organic phosphorous compound can be used at 0.001 to 100 molar equivalents with respect to compound (1-4), which is preferably 1 to 10 molar equivalents. Examples of phosphorane compounds include (cyanomethylene)tributylphosphorane, (cyanomethylene)trimethylphosphorane, and the like. A phosphorane compound can be used at 0.001 to 100 molar equivalents with respect to compound (1-4), which is preferably 1 to 10 molar equivalents. The reaction temperature is selected from the range of about −10° C. to about 100° C.

Step 1-3-2: If Y is an oxygen atom, a sulfur atom, or —NR^(j)— and T is a leaving group (e.g., a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as a methanesulfonyloxy group, a trihalogenomethanesulfonyloxy group such as a trifluoromethanesulfonyloxy group, an arylsulfonyloxy group such as a benzenesulfonyloxy group or p-toluenesulfonyloxy group, or the like), compound (1-6) can be manufactured by reacting compound (1-4) with compound (1-5) in an inert solvent, in the presence of a base under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THF and DME, halogenated hydrocarbon solvents such as dichloromethane and dichloroethane, aprotic solvents such as N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), and dimethyl sulfoxide (DMSO), and the like. Examples of bases include potassium tert-butoxy, sodium hydride, triethylamine, diisopropylethylamine, potassium carbonate, sodium carbonate, cesium carbonate, and the like. A base can be used at 0.001 to 100 molar equivalents with respect to compound (1-1), which is preferably 0.5 to 10 molar equivalents. Compound (1-5) can be used at 0.001 to 100 molar equivalents with respect to compound (1-4), which is preferably 1 to 10 molar equivalents. The reaction temperature is selected from the range of about −10° C. to about 100° C.

Step 1-4: This reaction can manufacture a compound from a corresponding compound (1-6) in accordance with a known method (e.g., WO 2014/151958, WO 2015/191907, WO 2016/003929, or the like). Preferably, a compound can be manufactured using Manufacturing Method (1-4-1) or Manufacturing Method 1-4-2) described below.

Manufacturing Method (1-4-1): Compound (1-7) can be manufactured by using compound (1-6) as a starting material and reacting the compound with boronic acid under acidic conditions in an inert solvent. Examples of boronic acid include phenylboronic acid and 2-methylpropyl boronic acid. The boronic acid can be used in the range of 0.001 to 100 equivalents with respect to compound (1-6), which is preferably 1 to 3 equivalents. Examples of acids include hydrochloric acid, trifluoroacetic acid, and the like. An acid can be used in the range of 0.001 to 100 equivalents with respect to compound (1-6), which is preferably 1 to 10 equivalents. Specific examples of inert solvents include halogenated hydrocarbon solvents such as dichloromethane and dichloroethane, hydrocarbon solvents such as hexane and heptane, ether solvents such as THF and CPME, nitrile solvents such as acetonitrile and propionitrile, and water, which can be used alone or as a mixture solvent. The acids described above can also be directly used as a solvent. A mixture solvent of hexane/acetonitrile is preferably used as a solvent. The reaction temperature is selected from the range of about −10° C. to about 100° C.

Manufacturing Method (1-4-2): Compound (1-7) can be manufactured by using compound (1-6) as the starting material and reacting the compound with triethylsilane in a trifluoroacetic acid solvent. Triethylsilane can be used in the range of 0.001 to 100 equivalents with respect to compound (1-6), which is preferably 1 to 50 equivalents. The reaction temperature is selected from the range of about −10° C. to about 70° C.

Manufacturing Method 1A

A compound of formula (1a) can be purchased or manufactured from a preparable corresponding material in the same manner as the manufacturing method of compound (1-7) described above. The compound is obtained in some cases as a compound of formula (1b), for example, by reacting with a reagent that generates nucleophilic X⁻ (X anion) (e.g., alkali metal salt generating a hydroxide anion HO⁻, alkali metal salt of C₁₋₆ alkoxide generating a C₁₋₆ alkoxide anion, the alkali metal salt of amide generating amide anion R^(a2)R^(b1)N⁻, or the like), depending on the property of compound (1a).

wherein X, Z, L¹, L², R¹, R², R³, and R⁴ are defined the same as item 1.

For example, a compound of formula (1a′) which is a compound of formula (1a) wherein X is a hydroxyl group, is obtained in some cases as a sodium salt compound of formula (1b′), depending on the property of the compound, by treatment with an aqueous sodium hydroxide solution.

wherein Z, L¹, L², G, R¹, R², R³, and R⁴ are defined the same as item 1.

For example, a compound of formula (1a″), which is a compound of formula (1a) wherein X is a hydroxyl group and R⁴ is a carboxyl group, is obtained in some cases as a disodium salt compound of formula (1b″), depending on the property of the compound, by treatment with an aqueous sodium hydroxide solution.

wherein Z, L¹, L², G, R¹, R², and R³ are defined the same as item 1. Manufacturing Method 2

Compounds of formula (1a) represented by formula (2-7) described below can be manufactured, for example, by the manufacturing method described below. Compound (2-7) represents compound (1-7) wherein L¹ is —NR^(d)(C═O)— and R^(d) is a hydrogen atom.

wherein L², Y, Z, ring A, L³, L¹, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, T, LG, PG¹, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1, and TMS represents a trimethylsilyl group.

A commercially available product that is purchased or a compound manufactured by the method described in Manufacturing Method 1 can be used as the starting material compound (1-1) and compound (1-5). Further, a commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (2-2) and compound (2-3). As compound (1-5), compound (2-2), and compound (2-3), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 2-1: Compound (2-1) can be manufactured by reacting compound (1-1) with hexamethyldisilazane lithium in an inert solvent under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and diethyl ether, and the like. Hexamethyldisilazane lithium can be used at 0.001 to 100 equivalents with respect to compound (1-1), which is preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 50° C.

Step 2-2: Compound (2-4) can be manufactured by reacting compound (2-1) with compound (2-2) or (2-3) in an inert solvent in the presence or absence of a condensing agent and/or base under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and DME, halogenated hydrocarbon solvents such as dichloromethane and chloroform, aprotic solvents such as DMF, NMP, and DMSO, and the like. (2-2) or (2-3) can be used at 0.001 to 100 equivalents with respect to compound (2-1), which is preferably 1 to 10 equivalents. Various condensing agents that are used in a conventional method can be used as the condensing agent. Examples thereof include 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (including hydrochloride), 0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, N,N′-dicyclohexylcarbodiimide, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, hydrates thereof, and the like. A condensing agent can be used at 0.001 to 100 equivalents with respect to compound (2-1), which is preferably 1 to 10 equivalents. Examples of bases include diisopropylethylamine, triethylamine, and the like. A base can be used at 0.001 to 100 equivalents with respect to compound (2-1), which is preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

Step 2-3: Compound (2-5) can be manufactured by using compound (2-4) as a starting material and using conditions in accordance with step 1-2 of Manufacturing Method 1 described above.

Step 2-4: Compound (2-6) can be manufactured by using compound (2-5) as a starting material, and reacting the compound with compound (1-5) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step 2-5: Compound (2-7) can be manufactured by using compound (2-6) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 3

A compound of formula (1a) represented by formula (3-7) described below can be manufactured, for example, by the manufacturing method described below.

wherein L¹, L², Z, L³, L¹, G, R, R, R, and R⁵ are defined the same as item 1, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, T, LG, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1, PG⁵ represents a protecting group of an amino group (e.g., an ethoxycarbonyl group, tert-butoxycarbonyl group, acetyl group, benzoyl group, trifluoroacetyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, triphenylmethyl group, methanesulfonyl group, p-toluenesulfonyl group, trimethylsilyl group, benzyloxycarbonyl group, 3- or 4-chlorobenzyloxycarbonyl group, benzylsulfonyl group, benzyl group, 4-nitrobenzyl group, 4-methoxybenzyl group, methyl group, ethyl group, or the like), and J represents a hydroxyl group or a leaving group (e.g., a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy, or the like).

A commercially available product that is purchased or a compound manufactured by the methods described in Manufacturing Method 1 and Manufacturing Method 2 can be used as the starting material compound (3-1) and compound (3-2). Further, a commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (3-2) and compound (3-5). As compound (3-2) and compound (3-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 3-1: Compound (3-3) can be manufactured by using compound (3-1) as a starting material, and reacting the compound with compound (3-2) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step 3-2: Compound (3-4) can be manufactured by deprotecting the protecting group PG⁵ of compound (3-3). This step can be performed in accordance with the method described in, for example, the document (T. W. Greene and P. G. M. Wuts, “Protective Group in Organic Synthesis”, 3^(rd) Ed., John Wiley and Sons, Inc., New York (1999)) or the like.

Step 3-3: Compound (3-6) can be manufactured by using compound (3-4) as a starting material and using conditions in accordance with step 2-2 of Manufacturing Method 2 described above.

Step 3-4: Compound (3-7) can be manufactured by using compound (3-6) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 4

A compound of formula (1a) represented by formula (4-4) described below can be manufactured, for example, by the manufacturing method described below.

wherein Y, ring A, L³, L⁴, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and T, PG¹, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1.

A commercially available product that is purchased or a compound manufactured by the method described in Manufacturing Method 1 can be used as the starting material compound (4-1) and compound (1-5). As compound (1-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 4-1: Compound (4-2) can be manufactured by using compound (4-1) as a starting material and using conditions in accordance with step 1-2 of Manufacturing Method 1 described above.

Step 4-2: Compound (4-3) can be manufactured by using compound (4-2) as a starting material, and reacting the compound with compound (1-5) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step 4-3: Compound (4-4) can be manufactured by using compound (4-3) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 5

A compound of formula (1a) represented by formula (5-4) described below can be manufactured, for example, by the manufacturing method described below.

wherein L³, L⁴, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, T, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1, and PG⁵ and J are defined the same as the definitions described in Manufacturing Method 3.

A commercially available product that is purchased or a compound manufactured by the methods described in Manufacturing Method 1 and Manufacturing Method 3 can be used as the starting material compound (4-1), compound (3-2), and compound (3-5). As compound (3-2) and compound (3-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 5-1: Compound (5-1) can be manufactured by using compound (4-1) as a starting material, and reacting the compound with compound (3-2) by using conditions in accordance with step 3-1 of Manufacturing Method 3 described above.

Step 5-2: Compound (5-2) can be manufactured by using compound (5-1) as a starting material and using conditions in accordance with step 3-2 of Manufacturing Method 3 described above.

Step 5-3: Compound (5-3) can be manufactured by using compound (5-2) as a starting material, and reacting the compound with compound (3-5) by using conditions in accordance with step 3-3 of Manufacturing Method 3 described above.

Step 5-4: Compound (5-4) can be manufactured by using compound (5-3) as a starting material and using conditions in accordance with step 3-4 of Manufacturing Method 3 described above.

Manufacturing Method 6

A compound of formula (1a) represented by formula (6-5) described below can be manufactured, for example, by the manufacturing method described below.

wherein L¹, L², Y, Z, ring A, L³, L⁴, G, R⁴, and R⁵ are defined the same as item 1, wherein one end of Y, R^(1a), and R^(2a) each attach to one of three attachable positions denoted as unsubstituted on a benzene ring in the chemical formula, R^(1a) and R^(2a) represent the remaining two without a structure of formula (2) among R¹, R², and R³ defined in item 1 herein, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and T, LG, PG¹, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1.

A commercially available product that is purchased or a compound manufactured by the method of Manufacturing Method 1 can be used as the starting material compound (6-1), compound (1-2), and compound (1-5). As compound (3-2) and compound (3-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step (6-1): Compound (6-2) can be manufactured by using compound (6-1) as a starting material, and reacting the compound with compound (1-2) by using conditions in accordance with step 1-1 of Manufacturing Method 1 described above.

Step (6-2): Compound (6-3) can be manufactured by using compound (6-2) as a starting material and using conditions in accordance with step 1-2 of Manufacturing Method 1 described above.

Step (6-3): Compound (6-4) can be manufactured by using compound (6-3) as a starting material, and reacting the compound with compound (1-5) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step (6-4): Compound (6-5) can be manufactured by using compound (6-4) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 7

A compound of formula (1a) represented by formula (7-5) described below can be manufactured, for example, by the manufacturing method described below. Said compound represents compound (6-5) wherein L¹ is —NR^(d)(C═O)— and R^(d) is a hydrogen atom.

wherein L², Y, Z, ring A, L³, L⁴, G, R⁴, and R⁵ are defined the same as item 1, wherein one end of Y, R^(1a), and R^(2a) each attach to one of three attachable positions denoted as unsubstituted on a benzene ring in the chemical formula, R^(1a) and R^(2a) represent the remaining two without a structure of formula (2) among R¹, R², and R³ defined in item 1 herein, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, T, LG, PG¹, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1, and TMS represents trimethylsilyl. A commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Trans formations”, 2^(nd) Ed., John Wiley and Son s, Inc., New York (1999) or the like) from a known compound can be used as compound (2-2) and compound (2-3). As compound (2-2), compound (2-3), or compound (1-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 7-1: Compound (7-1) can be manufactured by using compound (6-1) as a starting material and using conditions in accordance with step 2-1 of Manufacturing Method 2 described above.

Step 7-2: Compound (7-2) can be manufactured by using compound (7-3) as a starting material, and reacting the compound with compound (2-2) or compound (2-3) by using conditions in accordance with step 2-2 of Manufacturing Method 2 described above.

Step 7-3: Compound (7-3) can be manufactured by using compound (7-2) as a starting material and using conditions in accordance with step 2-3 of Manufacturing Method 2 described above.

Step 7-4: Compound (7-4) can be manufactured by using compound (7-3) as a starting material, and reacting the compound with compound (1-5) by using conditions in accordance with step 2-4 of Manufacturing Method 2 described above.

Step 7-5: Compound (7-5) can be manufactured by using compound (7-4) as a starting material and using conditions in accordance with step 2-5 of Manufacturing Method 2 described above.

Manufacturing Method 8

A compound of formula (1a) represented by formula (8-4) described below can be manufactured, for example, by the manufacturing method described below.

where L¹, L², Z, L³, L⁴, G, R⁴, and R⁵ are defined the same as item 1, wherein one end of an oxygen atom, R^(1a), and R^(2a) for substitution on a benzene ring each attach to one of three attachable positions denoted as unsubstituted on a benzene ring in the chemical formula, R^(1a) and R^(2a) represent the remaining two without a structure of formula (2) among R¹, R², and R³ defined in item 1 herein, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, T, PG², PG³, and PG⁴ are each defined the same as the definitions described in Manufacturing Method 1, and PG⁵ and J are each defined the same as the definitions described in Manufacturing Method 3.

A commercially available product that is purchased or a compound manufactured by the methods described in Manufacturing Method 1 and Manufacturing Method 2 can be used as the starting material compound (6-3). Further, a commercially available product that is purchased or a compound manufactured by the method described in Manufacturing Method 3 can be used as compound (3-2) and compound (3-5). As compound (3-2) and compound (3-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 8-1: Compound (8-1) can be manufactured by using compound (6-3) as a starting material, and reacting the compound with compound (3-2) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step 8-2: Compound (8-2) can be manufactured by using compound (8-1) as a starting material and using conditions in accordance with step 3-2 of Manufacturing Method 3 described above.

Step 8-3: Compound (8-3) can be manufactured by using compound (8-3) as a starting material, and reacting the compound with compound (3-5) by using conditions in accordance with step 3-3 of Manufacturing Method 3 described above.

Step 8-4: Compound (8-4) can be manufactured by using compound (8-3) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 9

A compound of formula (1a) represented by formula (9-4) described below can be manufactured, for example, by the manufacturing method described below.

wherein Y, ring A, L³, L⁴, C, R⁴, and R⁵ are defined the same as item 1, wherein one end of Y, R^(1a), and R^(2a) each attach to one of three attachable positions denoted as unsubstituted on a benzene ring in the chemical formula, R^(1a) and R^(2a) represent the remaining two without a structure of formula (2) among R¹, R², and R³ defined in item 1 herein, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and T, LG, PG¹, PG², PG³, and PG⁴ are each defined the same as the definition described in Manufacturing Method 1.

A commercially available product that is purchased or a compound manufactured by the method described in Manufacturing Method 1 can be used as the starting material compound (9-1) and compound (1-5). As compound (1-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 9-1: Compound (9-2) can be manufactured by using compound (9-1) as a starting material and using conditions in accordance with step 1-2 of Manufacturing Method 1 described above.

Step 9-2: Compound (9-3) can be manufactured by using compound (9-2) as a starting material, and reacting the compound with compound (1-5) by using conditions in accordance with step 1-3 of Manufacturing Method 1 described above.

Step 9-3: Compound (9-4) can be manufactured by using compound (9-3) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 10

A compound of formula (1a) represented by formula (10-4) described below can be manufactured, for example, by the manufacturing method described below.

wherein L³, L^(x), G, R⁴, and R⁵ are defined the same as item 1, T, PG², PG³, and PG⁴ are each defined the same as the definitions described in Manufacturing Method 1, wherein one end of an oxygen atom, Ra, and R^(a) for substitution on a benzene ring each attach to one of three attachable positions denoted as unsubstituted on a benzene ring in the chemical formula, R^(1a) and R^(2a) represent the remaining two without a structure of formula (2) among R¹, R², and R³ defined in item 1 herein, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and PG⁵ and J are defined the same as the definitions described in Manufacturing Method 3.

A commercially available product that is purchased or a compound manufactured by the methods described in Manufacturing Method 1 and Manufacturing Method 3 can be used as the starting material compound (9-2), compound (3-2), and compound (3-5). As compound (3-2) and compound (3-5), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 10-1: Compound (10-1) can be manufactured by using compound (9-2) as a starting material, and reacting the compound with compound (3-2) by using conditions in accordance with step 3-1 of Manufacturing Method 3 described above.

Step 10-2: Compound (10-2) can be manufactured by using compound (10-1) as a starting material and using conditions in accordance with step 3-2 of Manufacturing Method 3 described above.

Step 10-3: Compound (10-3) can be manufactured by using compound (10-2) as a starting material, and reacting the compound with compound (3-5) by using conditions in accordance with step 3-3 of Manufacturing Method 3 described above.

Step 10-4: Compound (10-4) can be manufactured by using compound (10-3) as a starting material and using conditions in accordance with step 3-4 of Manufacturing Method 3 described above.

Manufacturing Method 11

A compound of formula (1a) represented by formula (11-3) described below can be manufactured, for example, by the manufacturing method described below. Said compound (11-3) represents compound (3-7) wherein L³ is —S(═O)₂—.

wherein L¹, L², Z, L⁴, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and PG², PG³, and PG⁴ are each defined the same as the definitions described in Manufacturing Method 1.

A compound manufactured by the method described in Manufacturing Method 3 can be used as the starting material compound (3-4). Further, a commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (11-1). As compound (11-1), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 11-1: Compound (11-2) can be manufactured by reacting compound (3-4) with compound (11-1) in an inert solvent in the presence or absence of a base under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and DME, halogenated hydrocarbon solvents such as dichloromethane and chloroform, and aprotic solvents such as DMF, NMP, and DMSO. Compound (11-1) can be used at 0.001 to 100 equivalents with respect to compound (3-4), which is preferably 1 to 10 equivalents. Examples of bases include diisopropylethylamine, triethylamine, and the like. A base can be used at 0.001 to 100 equivalents with respect to compound (3-4), which is preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

Step 11-2: Compound (11-3) can be manufactured by using compound (11-2) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 12

A compound of formula (1a) represented by formula (12-2) described below can be manufactured, for example, by the manufacturing method described below. Said compound (12-2) represents compound (5-4) wherein L³ is —S(═O)₂—.

wherein L⁴, G, R¹, R², R⁴, and R⁵ are defined the same as item 1, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, and PG², PG³, and PG⁴ are each defined the same as the definitions described in Manufacturing Method 1.

A compound manufactured by the method described in Manufacturing Method 5 can be used as the starting material compound (5-2). Further, a commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (11-1). As compound (11-1), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 12-1: Compound (12-1) can be manufactured by using compound (5-4) as a starting material and using conditions in accordance with step 11-1 of Manufacturing Method 11 described above.

Step 12-2: Compound (12-2) can be manufactured by using compound (12-1) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

Manufacturing Method 13

A compound of formula (1a) represented by formula (13-5) described below can be manufactured, for example, by the manufacturing method described below. Said compound (13-5) represents compound (5-4) wherein R⁵ is optionally substituted 1H-1,2,3-triazole.

wherein L³, L⁴, G, R¹, R², and R⁴ are defined the same as item 1, m and n are defined the same as item 28, X^(a) is a hydroxyl group or a C₁₋₆ alkoxy group, H is a hydrogen atom, U represents an amino group, a nitro group, carboxylic acid, alcohol, or a leaving group (e.g., a halogen atom such as chlorine, bromine, or iodine, a lower alkylsulfonyloxy group such as methanesulfonyloxy, a trihalogenomethanesulfonyloxy group such as trifluoromethanesulfonyloxy, an arylsulfonyloxy group such as benzenesulfonyloxy or p-toluenesulfonyloxy, or the like), R^(p) is a group that is acceptable as a compound of formula (13-4) in R^(a) defined in item 36 or a group that can be converted into the R^(a), PG², PG³, and PG are each defined the same as the definitions described in Manufacturing Method 1, and J is defined the same as the definition described in Manufacturing Method 3.

A compound manufactured by the method described in Manufacturing Method 5 can be used as the starting material compound (5-2). Further, a commercially available product that is purchased or a compound synthesized in accordance with a known method (e.g., the method described in R. C. Larock, “Comprehensive Organic Transformations”, 2^(nd) Ed., John Wiley and Sons, Inc., New York (1999) or the like) from a known compound can be used as compound (13-1). As compound (13-1), a salt thereof can also be used, and the compound with a functional group that is protected can also be used as needed, as long as the reaction is not affected.

Step 13-1: Compound (13-2) can be manufactured using compound (5-4) as a starting material and using conditions in accordance with step 5-3 of Manufacturing Method 5 described above.

Step 13-2: Compound (13-3) can be manufactured by reacting compound (13-2) with an aziding agent in an inert solvent in the presence or absence of a base under normal pressure. Specific examples of inert solvents include halogenated hydrocarbon solvents such as dichloromethane and chloroform and aprotic solvents such as DMF, NMP, and DMSO. Specific examples of aziding agents include sodium azide, trimethylsilyl azide, diphenylphosphoryl azide, and the like. An aziding agent can be used at 0.001 to 100 equivalents with respect to compound (13-2), which is preferably 1 to 10 equivalents. Examples of bases include diisopropylethylamine, triethylamine, 4-dimethylaminopyridine, and the like. A base can be used at 0.001 to 100 equivalents with respect to compound (13-2), which is preferably 1 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

Step 13-3: Compound (13-5) can be manufactured by reacting compound (13-3) with compound (13-4) in an inert solvent in the presence or absence of a base in the presence or absence of a catalyst under normal pressure or under pressure. Specific examples of inert solvents include ether solvents such as THE and DME, halogenated hydrocarbon solvents such as dichloromethane and chloroform, and aprotic solvents such as acetonitrile, DMF, NMP, and DMSO. Compound (13-4) can be used at 0.001 to 100 equivalents with respect to compound (13-3), which is preferably 1 to equivalents. Examples of bases include diisopropylethylamine, triethylamine, and the like. A base can be used at 0.001 to 100 equivalents with respect to compound (13-3), which is preferably 1 to 10 equivalents. Specific examples of catalysts include copper sulfate, copper iodide, and (chloro[(1,2,3,4,5-h)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]bis(triphenylphosphine)ruthenium(II). A catalyst can be used at 0.001 to 100 equivalents with respect to compound (13-3), which is preferably 0.01 to 10 equivalents. The reaction temperature is selected from the range of about −78° C. to about 100° C.

Step 13-4: Compound (12-6) can be manufactured using compound (12-5) as a starting material and using conditions in accordance with step 1-4 of Manufacturing Method 1 described above.

The intermediate and compound of interest in the manufacturing methods described above can be isolated and purified by subjecting them to a purification method that is commonly used in organic synthesis chemistry (e.g., neutralization, filtration, extraction, washing, drying, concentration, recrystallization, various chromatography, or the like). Each intermediate can also be subjected to the subsequent reaction without any particular purification.

Optically active forms of the compound of the invention can be manufactured by using an optically active starting material or intermediate, or by optically resolving a racemate of the final product or intermediate. Examples of optional resolution methods include, but are not limited to, separation method using an optically active column and a separation method such as fractional crystallization method. A diastereomer of the compound of the invention can be manufactured by, for example, a separation method such as column chromatography or fractional crystallization, but the method is not limited thereto.

A pharmaceutically acceptable salt of a compound represented by formula (1a) or (1b) can be manufactured by, for example, mixing a compound represented by formula (1) with a pharmaceutically acceptable acid or base in a solvent such as water, methanol, ethanol, 2-propanol, ethyl acetate, or acetone, but the manufacturing method is not limited thereto.

As used herein, “or” is used when “at least one or more” of the listed matters in the sentence can be employed. When explicitly described herein as “within the range of two values”, the range also includes the two values themselves.

Reference literatures such as scientific literatures, patents, and patent applications cited herein are incorporated herein by reference to the same extent that the entirety of each document is specifically described.

The present invention has been described while showing preferred embodiments to facilitate understanding. While the present invention is described hereinafter based on the Examples, the above descriptions and the following Examples are provided for the sole purpose of exemplification, not limitation of the present invention. Thus, the scope of the present invention is not limited to the embodiments and Examples that are specifically described herein and is limited only by the scope of claims.

EXAMPLES

While the present invention is described more specifically with Reference Examples, Examples, and Test Examples hereinafter, the preset invention is not limited thereto.

Compounds were identified using proton nuclear magnetic resonance spectrum (¹H-NMR), liquid chromatography-mass spectrometry (LCMS), or the like. Tetramethylsilane was used as an internal standard for nuclear magnetic resonance spectrum.

For column chromatography in the Reference Examples and Examples, Yamazen Corporation's silica gel column, YMC's ODS-A column, and YMC's YMC-Actus Triart C18 were used. For TLC (silica gel plate) in purification using a thin layer chromatography (TLC), Silica gel 60F254 (Merck) was used, and for TLC (NH silica gel plate), TLC plate NH (Fuji Silysia) was used.

Various data described in the Reference Examples and Example was obtained with the following equipment.

NMR spectrum: [¹H-NMR] 400 MHz: JEOL JNM-AL series AL400, JEOL EX270, and 500 MHz: JEOL ECA-500.

600 Hz: Agilent DD2 600 MHz NMR Spectrometer.

LC-MS spectrum: Waters ACQUITY™ UltraPerformance LC, Waters AQUITY UPLC H-Class System, Shimadzu LCMS-2020.

The compound names described in the Reference Examples and Examples were named using ACD/Name (ACD/Labs 12.0, Advanced Chemistry Development Inc.), which are not necessarily in accordance with the IUPAC nomenclature.

The measuring conditions (hereinafter, also referred to as the measurement methods) for a high performance liquid chromatography-mass spectrometry (LCMS) system are described below. The observed mass spectrometry value [MS(m/z)] is indicated by [M+1]⁺, and the time of retention at which the mass spectrometry value was observed is indicated by Rt (min). The measurement conditions A to C used for measurement are denoted in each actual measurement value. For example, “LCMS: [M+H]⁺/Rt=620/1.32^(A)” expresses that measurement was taken under measurement condition A.

Measurement Condition A

Measuring equipment: Waters ACQUITY™ UltraPerformance LC

Column: ACQUITY UPLC BEH C18 1.7 μm 2.1×30 mm column

Solvent: solution A: 0.05% HCOOH/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.3 minutes; A/B=90/10 to 5/95 (linear gradient)

1.3 to 1.5 minutes; A/B=90/10

Flow rate: 0.80 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition B

Measuring equipment: Waters AQUITY UPLC H-Class System

Column: Waters AQUITY UPLC HSS T3 1.8 μm 2.1×50 mm column

Solvent: solution A: 0.1% HCO₂H/H₂O, solution B: 0.1% HCO₂H/MeCN

Gradient condition:

0.0 to 2.4 minutes; A/B=90/10 to 0/100 (linear gradient)

2.4 to 3.2 minutes; A/B=0/100

Flow rate: 0.70 mL/min

UV: 190 to 800 nm

Column temperature: 40° C.

Measurement Condition C

Measuring equipment: Waters ACQUITY™ UltraPerformance LC

Column: ACQUITY UPLC BEH C18 1.7 μm 2.1×30 mm column

Solvent: solution A: 0.05% HCOOH/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.3 minutes; A/B=99/1 to 5/95 (linear gradient)

1.3 to 1.5 minutes; A/B=99/1

Flow rate: 0.80 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition D

Measuring equipment: Waters AQUITY UPLC H-Class System

Column: ACQUITY UPLC BEH C18 1.7 μm 2.1×50 mm column

Solvent: solution A: HCOOH/CH₃CN/H₂O (0.05/50/49.95), solution B: 0.05% HCOOH/CH₃CN

Gradient condition: 0.0 to 4.0 minutes; A/B=100/0 to 0/100 (linear gradient)

4.0 to 5.0 minutes; A/B=0/100

Flow rate: 0.50 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition E

Measuring equipment: Waters ACQUITY™ UltraPerformance LC

Column: ACQUITY UPLC BEH C18 1.7 μm 2.1×30 mm column

Solvent: solution A: 0.05% HCOOH/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.3 minutes; A/B=60/40 to 5/95 (linear gradient)

1.3 to 1.5 minutes; A/B=60/40

Flow rate: 0.80 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition F

Measuring equipment: Waters ACQUITY™ UltraPerformance LC

Column: ACQUITY UPLC BEH C18 1.7 μm 2.1×30 mm column

Solvent: solution A: 0.05% HCOOH/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.3 minutes; A/B=98/2 to 4/96 (linear gradient)

1.3 to 1.5 minutes; A/B=98/2

Flow rate: 0.80 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition G

Measuring equipment: Shimadzu LCMS-2020

Column: Phenomenex Kinetex 1.7 μm C18 (50 mm×2.10 mm)

Solvent: solution A: 0.05% TFA/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.9 minutes; A/B=99/1 to 1/99 (linear gradient)

1.91 to 3.00 minutes; A/B=1/99

Flow rate: 0.50 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition H

Measuring equipment: Shimadzu LCMS-2020

Column: Phenomenex Kinetex 1.7 μm C18 (50 mm×2.10 mm)

Solvent: solution A: 0.05% TFA/H₂O, solution B: CH₃CN

Gradient condition:

0.0 to 1.9 minutes; A/B=90/10 to 1/99 (linear gradient)

1.91 to 3.00 minutes; A/B=1/99

Flow rate: 0.50 mL/min

UV: 220 nm, 254 nm

Column temperature: 40° C.

Measurement Condition I

Measuring equipment: Waters AQUITY™ UPLC H-Class System

Column: Waters AQUITY UPLC BEH C18 1.7 μm 2.1×50 mm column

Solvent: solution A: 0.05% HCO₂H/H₂O, solution B: 0.05% HCO₂H/MeCN

Gradient condition:

0.0 to 4.0 minutes; A/B=90/10 to 0/100 (linear gradient)

4.0 to 5.0 minutes; A/B=0/100

Flow rate: 0.50 mL/min

LTV: 220, 254 nm

Column temperature: 40° C.

The abbreviations described above and the following abbreviations are used in the Reference Examples, Examples, and Test Examples in some cases to simplify the description.

s: singlet

d: doublet

t: triplet

q: quadruplet

m: multiplet

br: broad

dd: double doublet

J: coupling constant

Hz: Hertz

δ: chemical shift

min: minute

THF: tetrahydrofuran

DMAP: N,N-dimethyl-4-aminopyridine

TFA: trifluoroacetic acid

DIPEA: N,N-diisopropylethylamine

DMF: dimethylformamide

DME: 1,2-dimethoxyethane

NMP: N-methylpyrrolidone

DMSO: dimethyl sulfoxide

Me: methyl

Et: ethyl

MeCN: acetonitrile

CPME: cyclopentyl methyl ether

Boc: tert-butoxycarbonyl

tBu or ^(t)Bu or t-Bu: tert-butyl

t-: tert-

Bn: benzyl

Cbz: benzyloxycarbonyl

Trt: trityl(triphenylmethyl)

Ms: methanesulfonyl, mesyl

HATU: 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate

N: normal

M: mol/L, molarity

MEPM: meropenem

MIC: minimum inhibitory concentration

Reference Example 1: Tert-butyl [1-(3-hydroxyazetidin-1-yl)ethylidene]carbamate

Reference Example 1-1: 3-bromo-2,6-dihydroxybenzoic Acid

N-bromosuccinimide (6.06 g, 34.1 mmol) was added in small portions to a dichloromethane solution (59 mL) of 2,6-dihydrobenzoic acid (5 g, 32.4 mmol) and N,N-diisopropylethylamine (2.27 mL, 16.2 mmol) at −78° C. The reaction solution was warmed up to room temperature, and stirred for 20 hours at said temperature. The reaction solution was evaporated under reduced pressure. 1 mol/L hydrochloric acid (40 mL) was added to the resulting residue, and the mixture was stirred for 30 minutes at room temperature. The precipitated crystals were filtered out, washed with water, and dried to obtain the title compound (6.03 g).

¹H-NMR (CDCl₃) δ: 7.58 (1H, d, J=9.2 Hz), 6.53 (1H, d, J=8.5 Hz).

LCMS: [M+H]⁺/Rt=233/0.412 min^(A)

Reference Example 1-2: Tert-butyl 3-bromo-2,6-bis[(tert-butoxycarbonyl)oxy]benzoate

Di-tert-butyl dicarbonate (65.2 g, 299 mmol) and DMAP (0.608 g, 4.98 mmol) were added to a THF (120 mL)/tert-butanol (60 mL) solution of the compound of Reference Example 1-1 (11.6 g, 49.8 mmol), and the reaction mixture was stirred for 18 hours at 60° C. The reaction solution was cooled to room temperature. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=99/1 to 95/5) to obtain the title compound (19.3 g).

¹H-NMR (CDCl₃) δ: 7.60 (1H, d, J=8.5 Hz), 7.02 (1H, d, J=8.5 Hz), 1.53 (9H, s), 1.51 (9H, s).

Reference Example 1-3: Tert-butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-ethenylbenzoate

Tri-n-butylvinyltin (2.04 mL, 6.95 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.488 g, 0.695 mmol) were added to a 1,4-dioxane (7 mL) solution of the compound of Reference Example 1-2 (1.7 g, 3.47 mmol) under a nitrogen atmosphere, and the reaction mixture was stirred for 10 hours at 110° C. After cooling the reaction solution to room temperature, the reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound (1.26 g).

¹H-NMR (CDCl₃) δ: 7.57 (1H, d, J=9.2 Hz), 7.11 (1H, d, J=8.5 Hz), 6.73 (1H, dd, J=17.7, 11.3 Hz), 5.74 (1H, d, J=17.7 Hz), 5.37 (1H, d, J=10.4 Hz), 1.57 (9H, s), 1.54 (9H, s), 1.52 (9H, s).

Reference Example 1-4: Tert-butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]benzoate

1,4-bis(diphenylphosphino)butane (0.547 g, 1.28 mmol), bis(1,5-cyclooctadiene)diiridium(I) dichloride (0.431 g,

0.641 mmol), and pinacolatodiboron (1.40 mL, 9.62 mmol) were added to a dichloromethane (32 mL) solution of the compound of Reference Example 1-3 (2.8 g, 6.41 mmol) under a nitrogen atmosphere, and the reaction mixture was stirred for 17 hours at room temperature. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound (3.59 g).

¹H-NMR (CDCl₃) δ: 7.30 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=8.5 Hz), 2.66-2.58 (2H, m), 1.53 (9H, s), 1.51 (9H, s), 1.51 (9H, s), 1.20 (12H, s), 1.10-1.02 (2H, m).

Reference Example 1-5: Tert-butyl 2,6-bis[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

(1S,2S,3R,5S)-(+)-pinanediol (0.736 g, 4.32 mmol) was added to a THF (5 mL) solution of the compound of Reference Example 1-4 (0.976 g, 1.73 mmol), and the reaction mixture was stirred for 62 hours at room temperature. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=99/1 to 85/15) to obtain the title compound (0.90 g).

¹H-NMR (CDCl₃) δ: 7.31 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=7.9 Hz), 4.23 (1H, dd, J=8.5, 1.8 Hz), 2.69-2.60 (2H, m), 2.35-2.24 (1H, m), 2.20-2.11 (1H, m), 2.04-1.97 (1H, m), 1.91-1.76 (2H, m), 1.54 (9H, s), 1.51 (18H, s), 1.34 (3H, s), 1.26 (3H, s), 1.14-1.07 (2H, m), 1.02 (1H, d, J=11.0 Hz), 0.81 (3H, s).

LCMS: [M−H]⁺/Rt=615/3.160 min^(B)

Reference Example 1-6: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-hydroxy-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Pyrrolidine (0.121 mL, 1.46 mmol) was added to a THE (5 mL) solution of the compound of Reference Example 1-5 (0.899 g, 1.46 mmol), and the reaction mixture was stirred for 3 hours at room temperature. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10 to 70/30) to obtain the title compound (0.68 g).

¹H-NMR (CDCl₃) δ: 11.26 (1H, s), 7.33 (1H, d, J=8.5 Hz), 6.82 (1H, d, J=8.5 Hz), 4.24 (1H, dd, J=8.8, 2.1 Hz), 2.63-2.54 (2H, m), 2.37-2.25 (1H, m), 2.23-2.11 (1H, m), 2.04-2.00 (1H, m), 1.93-1.78 (2H, m), 1.61 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.01 (3H, m), 0.83 (3H, s).

LCMS: [M−H]⁺/Rt=515/3.175 min^(B)

Reference Example 1-7: Benzyl 3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carboxylate

Under a nitrogen atmosphere, cesium carbonate (4.01 g) was added to a DMF (20.5 mL) solution of the compound of Reference Example 1-6 (2.117 g) and benzyl 3-iodoazetidine-1-carboxylic acid (1.95 g), and the reaction mixture was heated to 50° C. After 9 hours, the reaction mixture was cooled to room temperature. The reaction mixture was poured into water, extracted with a mixture solvent of ethyl acetate/hexane (1:1), and concentrated, and the residue was purified by using a silica gel column to obtain the title compound (2.46 g).

¹H-NMR (CDCl₃) δ: 7.36-7.26 (5H, m), 7.18 (1H, d, J=8.5 Hz), 6.36 (1H, d, J=8.5 Hz), 5.08 (2H, s), 4.91-4.84 (1H, m), 4.37-4.27 (2H, m), 4.24-4.18 (1H, m), 4.09-4.03 (2H, m), 2.58 (2H, t, J=8.2 Hz), 2.32-2.25 (1H, m), 2.18-2.08 (1H, m), 2.04-1.95 (1H, m), 1.89-1.84 (1H, m), 1.82-1.74 (1H, m), 1.53 (9H, s), 1.51 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.08 (2H, t, J=8.2 Hz), 1.00 (1H, d, J=11.0 Hz), 0.81 (3H, s).

Reference Example 1-8: Tert-butyl 6-[(azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate monohydrochloride

1 N hydrochloric acid (0.567 mL) and 50% water containing 10% palladium on carbon (0.149 g) were added to a methanol (16 mL) solution of the compound of Reference Example 1-7 (0.4 g), and the reaction mixture was stirred for 1 hour under hydrogen atmosphere. After celite filtration, the filtrate was concentrated to obtain the title compound (0.357 g).

¹H-NMR (CD₃OD) δ: 7.31 (1H, d, J=8.5 Hz), 6.66 (1H, d, J=8.5 Hz), 5.14 (1H, m), 4.55-4.42 (2H, m), 4.29-4.22 (1H, m), 4.13-4.05 (2H, m), 2.55 (2H, t, J=8.2 Hz), 2.35-2.30 (1H, m), 2.17-2.13 (1H, m), 1.99-1.92 (1H, m), 1.87-1.80 (1H, m), 1.79-1.72 (1H, m), 1.56 (9H, s), 1.50 (9H, s), 1.33 (3H, s), 1.27 (3H, s), 1.04 (2H, t, J=8.2 Hz), 0.98-0.96 (1H, m), 0.83 (3H, s).

Reference Example 1: Tert-butyl 6-[(1-acetylazetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Acetic anhydride (0.023 mL) and triethylamine (0.057 mL) were added to a THF (0.8 mL) solution of the compound of Reference Example 1-8 (0.1 g) in an ice bath, and the reaction mixture was stirred overnight at room temperature. After concentration, the mixture was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound (0.105 g).

¹H-NMR (CDCl₃) δ: 7.19 (1H, d, J=8.5 Hz), 6.39 (1H, d, J=8.5 Hz), 4.93-4.88 (1H, m), 4.46-4.30 (2H, m), 4.24-4.18 (1H, m), 4.16-4.00 (2H, m), 2.59 (2H, t, J=8.7 Hz), 2.35-2.23 (1H, m), 2.20-2.09 (1H, m), 2.01-1.96 (1H, m), 1.91-1.82 (4H, m), 1.82-1.73 (1H, m), 1.54 (9H, s), 1.49 (9H, d, J=15.8 Hz), 1.32 (3H, t, J=7.0 Hz), 1.25 (3H, s), 1.10 (2H, t, J=8.7 Hz), 1.03-0.97 (1H, m), 0.81 (3H, s).

Reference Example 2: Tert-butyl 6-[(1-methylsulfonylazetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 1 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 7.20 (1H, d, J=8.5 Hz), 6.41 (1H, d, J=8.5 Hz), 4.93-4.87 (1H, m), 4.29-4.20 (3H, m), 4.00-3.97 (2H, m), 2.89 (3H, s), 2.61-2.57 (2H, m), 2.33-2.26 (1H, m), 2.15 (1H, ddd, J=13.7, 6.1, 3.4 Hz), 2.00 (1H, t, J=5.5 Hz), 1.87 (1H, td, J=6.3, 3.9 Hz), 1.78 (1H, dt, J=14.6, 2.7 Hz), 1.55 (9H, s), 1.51 (9H, s) 1.34 (3H, s), 1.26 (3H, s), 1.11-1.06 (2H, m), 1.00 (2H, d, J=11.0 Hz), 0.81 (3H, s).

Reference Example 3: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

HATU was added to a DMF (0.905 mL) solution of the compound of Reference Example 1-8 (0.11 g), 4-imidazoleacetic acid hydrochloride (0.059 g), and triethylamine (0.076 mL) in an ice bath. The reaction mixture was slowly warmed up to room temperature, and stirred for 18 hours. The reaction mixture was poured into water, extracted with a mixture solvent of ethyl acetate/hexane (2:1), and concentrated, and the residue was purified by using a silica gel column to obtain the title compound (0.096 g).

¹H-NMR (CDCl₃) δ: 8.19 (1H, s), 7.21 (1H, d, J=8.5 Hz),

7.00 (1H, s), 6.39 (1H, d, J=8.5 Hz), 4.90 (1H, m), 4.61-4.59 (1H, m), 4.31-4.27 (1H, m), 4.23-21 (1H, m), 4.7-4.05 (1H, m), 3.81-78 (1H, m), 3.54 (2H, s), 2.58 (2H, m), 2.30-2.26 (2H, m), 2.17-2.13 (1H, m), 2.02-1.98 (1H, m), 1.88-1.87 (1H, n)d, 1.80-1.77 (1H, 8) 1.54 (9H, s), 1.51 (9H, s), 1.33 (9, s), 1.25 (3H, s), 1.10-1.06 (2H, in), 1.22-1.10 (1H, s), 0.81 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 3 to obtain each of Reference Example compounds 4 to 34 shown in Table 2.

TABLE 2-1 TABLE 2 Reference Example Structural formula NMR and/or LCMS  4

¹H-NMR (CDCl₃) δ: 7.31- 7.23 (18H, m), 7.19 (1H, d, J = 8.5 Hz), 6.96 (1H, s), 6.56 (1H, s), 6.35 (1H, d, J = 8.5 Hz), 4.93 (1H, ddd, J = 11.3, 5.8, 3.7 Hz), 4.46 (1H, dd, J = 11.0, 6.7 Hz), 4.32 (1H, dd, J = 9.2, 6.7 Hz), 4.22 (1H, dd, J = 8.5, 1.8 Hz), 4.16- 4.04 (3H, m), 4.01 (4H, t, J = 10.7 Hz), 2.59 (2H, t, J = 8.2 Hz), 2.33-2.26 (1H, m), 2.15 (1H, tt, J = 10.7, 3.5 Hz), 1.99 (3H, t, J = 5.8 Hz), 1.89-1.85 (1H, m), 1.78 (1H, dt, J = 14.6, 2.7 Hz), 1.65 (2H, t, J = 6.1 Hz), 1.55-1.46 (19H, m), 1.37-1.29 (4H, m), 1.27 (4H, d, J = 9.8 Hz), 1.07 (2H, dd, J = 15.3, 7.3 Hz), 1.01 (1H, t, J = 7.6 Hz), 0.81 (3H, s).  5

¹H-NMR (CDCl₃) δ: 8.54 (1H, d, = 4.3 Hz), 8.10 (1H, d, J = 7.9 Hz), 7.79- 7.77 (1H, m), 7.35-7.32 (1H, m), 7.21 (1H, d, J = 8.5 Hz), 6.44 (1H, d, = 8.5 Hz), 5.09-5.06 (1H, m), 4.98-4.97 (1H, m), 4.70-4.67 (1H, m), 4.58- 4.55 (1H, m), 4.30-4.19 (2H, m), 2.60 (2H, t, J = 8.2 Hz), 2.31-2.28 (1H, m), 2.18-2.13 (1H, m), 2.02- 1.99 (1H, m), 1.87 (1H, br s), 1.81-1.77 (1H, m), 1.53 (9H, s), 1.51 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.10 (2H, t, = 7.9 Hz), 1.01 (1H, d, J = 11.0 Hz), 0.81 (3H, s).  6

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.6 Hz), 6.42 (1H, d, J = 8.6 Hz), 5.30 (2H, s), 5.00-4.90 (1H, m), 4.60-4.52 (1H, m), 4.46- 4.36 (1H, m), 4.28-4.08 (4H, m), 3.07 (2H, s), 2.66- 2.58 (2H, m), 2.39-2.24 (1H, m), 2.22-2.12 (1H, m), 2.07-1.99 (1H, m), 1.93-1.76 (2H, m), 1.57 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14- 1.01 (3H, m), 0.84 (3H, s).

TABLE 2-2  7

¹H-NMR (CDCl₃) δ: 8.19 (1H, s), 7.24 (1H, d, J = 8.6 Hz), 6.46 (1H, d, J = 8.6 Hz), 5.18-5 00 (2H, m) 4.76-4.58 (2H, m), 4.14- 4.09 (2H, m), 2.62 (2H, t, J = 8.2 Hz), 2.38-2.25 (1H, m), 2.23-2.09 (1H, m), 2.07-1.99 (1H, m), 1.93- 1.75 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.34 (3H, s), 1.28 (3H, s), 1.12 (2H, t, J = 8.2 Hz), 1.07-1.00 (1H, m), 0.84 (3H, s).  8

¹H-NMR (CDCl₃) δ: 8.20- 8.17 (1H, m), 7.55-7.51 (1H, m), 7.38-7.12 (4H, m), 6.39 (1H, d, J = 8.6 Hz). 5.13-4.96 (1H, m), 4.77- 4.61 (2H, m), 4.28-4.23 (2H, m), 4.14-4.05 (1H, m), 2.72-2.55 (2H, m), 2.32- 2.25 (1H, m), 2.23-2.10 (1H, m), 2.07-1.98 (1H, m), 1.95-1.74 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.35 (3H, s), 1.28 (3H, 2), 1.13- 1.00 (3H, m), 0.83 (3H, s).  9

¹H-NMR (CDCl₃) δ: 7.43- 7.28 (4H, m), 7.23-7.14 (1H, m), 6.40-6.27 (1H, m), 5.97-5.78 (1H, m), 5.22- 5.10 (1H, m), 4.99-471 (1H, m), 4.65-4.37 (1H, m), 4.35-4.18 (2H, m), 4.18- 4.04 (1H, m), 4.04-3.77 (1H, m), 2.66-2.54 (2H, m), 2.38-2.24 (1H, m), 2.205-1.98 (1H, m), 1.94- 1.85 (1H, m), 1.84-1.74 (1H, m), 1.57 (9H, m), 1.54-1.48 (9H, m), 1.42- 1.36 (9H, m), 1.35 (3H, s), 1.28 (3H, s), 1.14-0.94 (1H, m), 0.83 (3H, s). 10

¹H-NMR (CDCl₃) δ: 7.67- 7.59 (2H, m), 7.50-7.36 (3H, m), 7.23-7.19 (1H, d, J = 8.6 Hz), 6.41 (1H, d, J = 8.6 Hz), 5.05-4.95 (1H, m), 4.64-4.50 2H, m), 4.39-4.30 (3H, m), 2.73- 2.55 (2H, m), 2.39-2.25 (1H, m), 2.25-2.09 (1H, m), 2.08-1.96 (1H, m), 1.95-1.75 (2H, m), 1.60- 1.75 (18H, m), 1.37-1.23 (6H, m), 1.22-0.96 (3H, m), 0.86-0.80 (3H, m). 11

LCMS: [M + H]⁺/Rt = 678/2.75 min^(B) 12

LCMS: [M + H]⁺/Rt = 692/2.62 min^(B)

TABLE 2-3 13

LCMS: [M + H]⁺/Rt = 692/2.53 min^(B) 14

LCMS: [M + H]⁺/Rt = 828/3.06 min^(B) 15

LCMS: [M + H]⁺/Rt = 692/2.79 min^(B) 16

¹H-NMR (CDCl₃) δ: 7.32- 7.26 (2H, m), 7.23-7.17 (1H, m), 7.16-7.00 (2H, m), 6.43-6.36 (1H, m), 4.95-4.86 (1H, m), 4.46- 4.30 (2H, m), 4.29-4.20 (1H, m), 4.18-4.06 (2H, m), 3.55-3.40 (2H, m), 2.68-2.55 (2H, m), 2.39- 2.24 (1H, m), 2.22-2.10 (1H, m), 2.08-1.98 (1H, m), 1.95-1.73 (2H, m), 1.62-1.49 (27H, m), 1.36 (3H, s), 1.28 (3H, m), 1.14-1.01 (3H, m), 0.83 (3H, s). 17

LCMS: [M + H]⁺/Rt = 922/3.08 min^(B) 18

LCMS: [M + H]⁺/Rt = 682/2.63 min^(B) 19

LCMS: [M + H]⁺/Rt = 852/3.06 min^(B)

TABLE 2-4 20

¹H-NMR (CDCl₃) δ: 7.37- 7.17 (6H, m), 6.42-6.34 (1H, m), 4.94-4.84 (1H, m), 4.44-4.32 (2H, m), 4.29- 4.19 (1H, m), 4.18-4.02 (2H, m), 3.50 (2H, s), 2.68- 2.54 (2H, m), 2.38-2.26 (1H, m), 2.24-2.10 (1H, m), 2.06-1.98 (1H, m), 1.95- 1.73 (2H, m), 1.54 (9H, s), 1.54 (9H, s) 1.36 (3H, s), 1.28 (3H, m), 1.13-1.00 (3H, m), 0.83 (3H, s). 21

LCMS: [M + H]⁺/Rt = 705/2.98 min^(B) 22

LCMS: [M + H]⁺/Rt = 681/2.22 min^(B) 23

LCMS: [M + H]⁺/Rt = 682/2.66 min^(B) 24

LCMS: [M + H]⁺/Rt = 683/2.62 min^(B) 25

LCMS: [M + H]⁺/Rt = 820/3.06 min^(B)

TABLE 2-5 26

LCMS: [M + H]⁺/Rt = 936/3.12 min^(B) 27

LCMS: [M + H]⁺/Rt = 810/2.20 min^(B) 28

LCMS: [M + H]⁺/Rt = 772/3.01 min^(B) 29

LCMS: [M + H]⁺/Rt = 810/2.20 min^(B) 30

LCMS: [M + H]⁺/Rt = 874/2.87 min^(B) 31

LCMS: [M + H]⁺/Rt = 770/3.01 min^(B)

TABLE 2-6 32

LCMS: [M + H]⁺/Rt = 770/3.01 min^(B) 33

LCMS: [M + H]⁺/Rt = 824/2.20 min^(B) 34

¹H-NMR (CD₃OD) δ: 7.34 (2H, d, J = 8.5 Hz), 7.30- 7.29 (3H, m), 7.22-7.20 (2H, m), 7.06 (1H, d, J = 8.5 Hz), 6.89 (2H, d, J = 8.5 H), 6.84 (2H, d, J = 8.5 Hz), 6.63 (1H, d, J = 8.5 Hz), 5.07 (2H, s), 5.06 (2H, s), 5.05-5.02 (1H, m), 4.52-4.49 (2H, m), 4.27 (1H, d, J = 7.3 Hz), 4.10-4.08 (2H, m), 3.77 (3H, s), 3.74 (3H, s), 2.57 (2H, t, J = 8.2 Hz), 2.34-2.31 (1H, m), 2.16- 2.15 (1H, m), 1.97 (1H, t, J = 5.5 Hz), 1.84 (1H, br s), 1.78-1.75 (1H, m), 1.53 (9H, s), 1.51 (9H, s), 1.33 (3H, s), 1.26 (3H, s), 1.07 (2H, t, J = 7.9 Hz), 0.96-0.94 (1H, m), 0.84 (3H, s).

Reference Example 35: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(hydroxycarbamoyl) azetidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Triphosgene (14.92 mg) was added to a toluene solution of the compound of Reference Example 1-8 (76.4 mg) and DIPEA (0.066 mL) at, 0° C. The reaction mixture was returned to room temperature and stirred for 1.5 hours. The reaction mixture was concentrated. DMF (2.5 mL), DIPEA (0.5 mL), and hydroxylamine hydrochloride (51 mg) were added to the residue, and the reaction mixture was stirred for 3 hours at room temperature. A saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was subjected to silica gel column chromatography to obtain the title compound (56.5 mg) as a colorless solid.

¹H-NMR (CDCl₃) δ: 7.12 (1H, d, J=8.5 Hz), 7.04 (1H, s), 7.00 (1H, br s), 6.33 (1H, d, J=8.5 Hz), 4.87-4.83 (1H, m), 4.34 (2H, dd, J=9.8, 6.7 Hz), 4.17 (1H, dd, J=8.5, 1.8 Hz), 4.06-4.01 (2H, m), 2.53 (2H, t, J=8.5 Hz), 2.28-2.21 (1H, m), 2.13-2.07 (1H, m), 1.95 (1H, t, J=5.5 Hz),

1.83-1.81 (1H, m), 1.75-1.72 (1H, m), 1.49 (9H, s), 1.46 (9H, s), 1.29 (3H, s), 1.21 (3H, s), 1.03 (2H, t, J=8.5 Hz), 0.96 (1H, d, J=10.4 Hz), 0.76 (3H, s).

Reference Example (R)-36: Tert-butyl 6-({1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate Reference Example (S)-36: Tert-butyl 6-({1-[(2R)-2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 36-1: 4-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide

Dimethylsulfamoyl chloride (91 mL, 859 mmol) was added dropwise to a chloroform solution (750 ml) of 1H-imidazole-4-carbaldehyde (75 g, 78 mmol) and triethylamine (163 mL, 1.17 mol) over 50 minutes at room temperature. The reaction solution was stirred for 3 days and then water (900 mL) was added, and the mixture was extracted with chloroform (500 mL, 3 times). The organic phase was dried over sodium sulfate, filtered, and concentrated to obtain the title compound (161 g) as a white solid with a brownish tinge.

¹H-NMR (CDCl₃) δ: 9.88 (1H, br s), 7.91 (1H, t, J=7.3 Hz),

7.84 (1H, dd, J=8.5, 1.2 Hz), 2.87 (6H, dd, J=9.8, 5.5 Hz).

Reference Example 36-2: amino(1H-imidazol-4-yl)acetic Acid Dihydrochloride

Sodium cyanide (46.7 g, 953 mmol) was added to an ethanol solution (227 mL) of the compound of Reference Example 36-1 (161 g, 794 mmol) and 28% aqueous ammonia (371 mL) while being cooled with ice (internal temperature of 14° C.). The reaction solution was stirred for 4 hours at room temperature and then extracted with chloroform (500 mL, 4 times). The organic phase was dried over sodium sulfate, filtered, and concentrated. 6 N aqueous hydrochloric acid (850 mL) was added to the resulting solid residue, and the reaction mixture was refluxed for 4 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid residue was stirred and washed with a THF-ethanol mixture solvent (1:1, 750 mL) and filtered to obtain the title compound (160 g) as a yellow solid with a brownish tinge.

¹H-NMR (D₂O) δ: 8.69 (1H, S), 7.54 (1H, s), 5.14 (1H, s).

Reference Example 36-3: [(tert-butoxycarbonyl)amino](1H-imidazol-4-yl)acetic Acid Hydrochloride

An aqueous 3 N sodium hydroxide solution (374 mL) was added dropwise to a methanol solution (194 mL) of the compound of Reference Example 36-2 (80 g, 374 mmol) over 45 minutes while cooling with ice. After stirring the reaction solution for 15 minutes while cooling with ice, di-tert-butyl dicarbonate was added over 15 minutes. The reaction solution was stirred for 45 minutes while cooling with ice and then warmed up to room temperature. To the reaction solution, N,N-dimethyl-4-aminopyridine (2.28 g, 18.7 mmol) and 2,2,2-trifluoroethanol (53.4 mL, 747 mmol) were added at room temperature, and the reaction solution was refluxed for 2 hours. After the reaction solution was allowed to cool down, 6 N aqueous hydrochloric acid (25 mL) was added while cooling with ice to adjust the pH of the solution to 6.0. After stirring for 1 hour while cooling with ice, the precipitated solid was filtered out, washed with acetone-water mixture solvent (1:1, 1 L), and dried and solidified under reduced pressure to obtain the title compound (40.0 g) as a white solid.

¹H-NMR (D₂O) δ: 8.50 (1H, d, J=1.2 Hz), 7.27 (1H, s), 5.04 (1H, s), 1.30 (9H, s).

Reference Example 36: Tert-butyl 6-({1-[2-({tert-butoxycarbonyl}amino)-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Triethylamine (1.54 ml, 11.1 mmol), 1-hydroxybenzotriazole (0.747 g, 5.53 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.689 g, 3.59 mmol) were added to a DMF solution (9.21 mL) of the compound of Reference Example 36-3 (1.0 g, 4.15 mmol) while cooling with ice. After stirring for 1 hour while cooling with ice, N,N-dimethyl-4-aminopyridine (0.068 g, 0.553 mmol) and the compound of Reference Example 1-8 (1.68 g, 2.76 mmol) were added to the reaction solution. After stirring for 24 hours at room temperature, an aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The organic phase was dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to obtain the title compound (1.09 g) as a while amorphous compound.

LCMS: [M+H]⁺/Rt=795.44/0.845 min^(E)

The compound of Reference Example 36 (amount charged per injection: 19.6 mg) was dissolved in 0.300 mL of ethyl acetate. Isomers were obtained by optical resolution by chiral chromatography under the following conditions. Column: CHIRALPAK IG 20 mmφ×250 mm (Daicel Corporation) Mobile phase: diethylamine/ethyl acetate (diethylamine: 0.1%)

Flow rate: 10 mL/min

Temperature: 40° C.

Column retention times for both optical isomers were as follows.

(R)-36: 6.056 min

(S)-36: 4.225 min

Reference Example 37: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](1-methyl-1H-imidazol-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 37-1: [(tert-butoxycarbonyl)amino](1-methyl-1H-imidazol-4-yl) Acetic Acid

Sodium hydrogen carbonate (1.09 g, 13.0 mmol) and di-tert-butyl dicarbonate (1.30 mL, 5.62 mmol) were added to a methanol/water (1:1, 8.6 mL) solution of amino(1-methyl-1H-imidazol-4-yl) acetic acid (670 mg, 4.32 mmol), and the reaction mixture was stirred at room temperature. After 2 hours, the reaction solution was concentrated, and the residue was dissolved in ethanol (17 mL). Potassium hydrogen sulfate (2.35 g) was added at 0° C. to quench the reaction. Solids were filtered out, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0 to 40/60) to obtain the title compound (400 mg) as a yellow solid.

LCMS: [M+H]⁺/Rt=255.94/0.419 min^(C)

Reference Example 37: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](1-methyl-1H-imidazol-4-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (325 mg, 0.535 mmol) and the compound of Reference Example 37-1 (205 mg, 0.803 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (130 mg).

LCMS: [M+H]⁺/Rt=809.58/1.246 min^(C)

Reference Example 38: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](2-methyl-1H-imidazol-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 38-1: [(tert-butoxycarbonyl)amino][1-(tert-butoxycarbonyl)-2-methyl-1H-imidazol-4-yl]acetic Acid

Di-tert-butyl dicarbonate (1.64 g, 7.52 mmol) was added to a methanol solution (10 mL) of methyl 2-amino-2-(2-methyl-1H-imidazol-4-yl)acetate dihydrochloride (0.828 g, 3.42 mmol), N,N-dimethyl-4-aminopyridine (0.084 g, 0.684 mmol), and triethylamine (1.91 mL, 13.7 mmol) at room temperature, and the reaction mixture was stirred. After the completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate and concentrated to obtain the title compound (0.59 g).

¹H-NMR (CD₃OD) δ: 7.31 (1H, s), 4.91 (1H, s), 2.53 (3H, s), 1.60 (9H, s), 1.42 (9H, s).

Reference Example 38-2: potassium [(tert-butoxycarbonyl)amino](2-methyl-1H-imidazol-4-yl)acetate

Potassium carbonate (0.331 g, 2.40 mmol) was added to a methanol solution (3.2 mL) of the compound of Reference Example 38-1 (0.59 g, 1.60 mmol). After stirring for 30 minutes at room temperature, the aqueous layer was washed with ethyl acetate and concentrated to obtain the title compound (0.47 g).

¹H-NMR (CD₃OD) δ: 6.77 (1H, s), 4.98 (1H, s), 2.29 (3H, s), 1.43 (9H, s).

Reference Example 38: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](2-methyl-1H-imidazol-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (0.328 g, 0.539 mmol) and the compound of Reference Example 38-2 (0.234 g, 0.799 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (68.3 mg).

LCMS: [M+H]⁺/Rt=809.50/1.162 min^(C)

Reference Example 39: Tert-butyl 6-[(1-{2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)propanoyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 39-1: Methyl amino(1H-imidazol-4-yl)acetate Dihydrochloride

Thionyl chloride (75 mL, 1.21 mol) was added dropwise to a methanol solution (265 mL) of the compound of Reference Example 36-2 (44 g, 206 mmol) while cooling with ice. The reaction solution was warmed up to room temperature and then stirred for 8 hours at 50° C. The reaction solution was concentrated under reduced pressure to obtain the title compound (46.9 g) as a light yellow oily substance.

LCMS: [M+H]⁺/Rt=155.93/0.142 min^(C)

Reference Example 39-2: Tert-butyl 4-{1-[(tert-butoxycarbonyl)amino]-2-methoxy-2-oxoethyl}-1H-imidazole-1-carboxylate

N,N-dimethyl-4-aminopyridine (0.113 g, 0.928 mmol), triethylamine (0.863 mL, 6.19 mmol), and di-tert-butyl dicarbonate (1.08 mL, 4.64 mmol) were added to a chloroform solution (20 mL) of the compound of Reference Example 39-1 (0.70 g, 3.09 mmol) at room temperature, and the reaction mixture was stirred for 24 hours. The reaction solution was concentrated and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound (1.10 g) as a colorless oily substance.

¹H-NMR (CD₃OD) δ: 8.14 (1H, d, J=1.2 Hz), 7.51 (1H, s), 5.27 (1H, s), 3.73 (3H, s), 1.63 (9H, s), 1.45 (9H, s).

Reference Example 39-3: Tert-butyl 4-{2-[(tert-butoxycarbonyl)amino]-1-methoxy-1-oxopropan-2-yl}-1H-imidazole-1-carboxylate

A lithium bis(trimethylsilyl)amide/THE solution (1.3 mol/L, 19.6 mL, 25.4 mmol) was added to a THF solution (43 mL) of the compound of Reference Example 39-2 (4.3 g, 12.1 mmol) at −78° C., and the reaction mixture was stirred for 30 minutes. Methyl iodide (0.832 mL, 13.3 mmol) was added to the reaction solution at −78° C. The reaction solution was warmed up to room temperature, and stirred for 4 hours. Saturated saline was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain the title compound (2.15 g) as a light yellow oily substance.

¹H-NMR (CDCl₃) δ: 8.00 (1H, d, J=1.2 Hz), 7.35 (1H, d, J=1.2 Hz), 6.08 (1H, s), 3.73 (3H, s), 1.91 (3H, s), 1.61 (9H, s), 1.43 (9H, s).

Reference Example 39-4: 2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)propanoic Acid

Lithium hydroxide monohydrate (0.513 g, 12.2 mmol) was added to a methanol solution (11.6 mL) of the compound of Reference Example 39-3 (2.15 g, 5.82 mmol) at room temperature, and the reaction mixture was stirred for 3 hours. 6 N aqueous hydrochloric acid (2.1 mL) was added, and the reaction mixture was stirred for 4 hours. Saturated saline was added to the reaction solution, and the solvent was evaporated under reduced pressure to obtain the title compound (1.49 g) as a crude product.

Reference Example 39: Tert-butyl 6-[(1-{2-[(tert-butoxycarbonyl)amino]-2-(1H-imidazol-4-yl)propanoyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (0.30 g, 0.493 mmol) and the compound of Reference Example 39-4 (0.176 g, 0.691 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (153 mg).

LCMS: [M+H]⁺/Rt=809.17/1.139 min^(C)

Reference Example 40: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3 mL) of the compound of Reference Example 1-7 (200 mg, 0.283 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in DMF (3 mL), and triethylamine (0.118 mL, 0.850 mmol) and 1H-imidazole-5-carboxylic acid chloride (40.7 mg, 0.312 mmol) were added. The reaction mixture was stirred for 20 minutes at room temperature, then water was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol) to obtain the title compound (149 mg) as a light yellow solid.

¹H-NMR (CDCl₃) δ: 7.77-7.55 (2H, m), 7.26-722 (1H, m), 7.46 (1H, d, J=8.1 Hz), 5.12-4.90 (2H, m), 4.66-4.40 (2H, m), 4.30-4.15 (2H, m), 2.65-2.59 (2H, m), 2.36-2.26 (1H, m), 2.23-2.13 (1H, m), 2.05-2.00 (1H, m), 1.92-1.70 (2H, m), 1.59 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.15-1.01 (311, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=666.7/2.49 min^(B)

Reference Example 41: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3 mL) of the compound of Reference Example 1-7 (200 mg, 0.283 mmol), and the reaction mixture was stirred for 30 minutes at room temperature under a hydrogen atmosphere. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in methylene chloride (3 mL), and triethylamine (0.118 mL, 0.850 mmol) was added. A methylene chloride solution (3 mL) of 1H-1,2,4-triazole-3-sulfonyl chloride (47.5 mg, 0.283 mmol) was added while cooling with ice, and the reaction mixture was stirred for 5 minutes. Water was added to the reaction solution, which was extracted with methylene chloride. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate) to obtain the title compound (205 mg) as a colorless solid.

¹H-NMR (CDCl₃) δ: 8.37 (1H, s), 7.20 (1H, d, J=8.1 Hz), 6.26 (1H, d, J=8.1 Hz), 4.43-4.37 (2H, m), 4.24 (1H, dd, J=8.1 Hz, 2.7 Hz), 4.16-4.08 (3H, m), 2.62-2.56 (2H, m), 2.36-2.27 (1H, m), 2.21-2.12 (1H, m), 2.05-2.00 (1H, m), 1.92-1.76 (2H, m), 1.55 (9H, s), 1.52 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.12-0.99 (3H, m), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=703.6/2.75 min^(B)

Reference Example 42: Tert-butyl 6-({1-[N²-(tert-butoxycarbonyl)-L-asparaginyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3 mL) of the compound of Reference Example 1-7 (200 mg, 0.283 mmol), and the reaction mixture was stirred for 30 minutes at room temperature under a hydrogen atmosphere. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in THE (3 mL), and tert-butoxycarbonyl-L-asparagine (85.6 mg, 0.368 mmol), N,N′-dicyclohexylcarbodiimide (58.5 mg, 0.340 mmol), 1-hydroxybenzotriazole monohydrate (52.1 mg, 0.340 mmol), and N-methylmorpholine (34.3 μL, 0.312 mmol) were added, and the reaction mixture was stirred for 2 hours at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate) to obtain the title compound (198 mg) as a colorless solid.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.41-6.37 (1H, m), 6.03 (1H, br), 5.72-5.61 (1H, m), 5.48-5.39 (1H, m), 4.99-4.89 (1H, m), 4.75-4.51 (2H, m), 4.44-4.31 (2H, m), 4.27-4.23 (1H, m), 4.10-4.03 (1H, m), 2.73-2.56 (4H, m), 2.36-2.27 (1H, m), 2.20-2.14 (1H, m), 2.04-2.00 (1H, m), 1.92-1.77 (2H, m), 1.57 (9H, s), 1.53 (9H, s), 1.43 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=786.8/2.79 min^(B)

Reference Example 43: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 43-1: tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(chloroacetyl)azetidin-3-yl]oxy}-3-{2-[(3aS, 4S, 6S, 7aR)-3a, 5, 5-trimethylhexahydro-2H -4, 6-methano-1, 3, 2-benzodioxaborol-2-yl]ethyl}benzoate

Under a nitrogen atmosphere, a dichloromethane (5.3 mL) solution of the compound of Reference Example 1-8 (160 mg, 0.263 mmol) was cooled with ice to 0° C. Chloroacetyl chloride (30 μL, 0.377 mmol) and triethylamine (0.11 mL, 0.789 mmol) were added, and the reaction mixture was stirred for 1 hour at room temperature. Subsequently, the reaction solution was cooled with ice, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous ammonium chloride solution and saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=1/1) to obtain the title compound (140 mg).

¹H-NMR (CDCl₃) δ: 7.21 (1H, d, J=8.6 Hz), 6.40 (1H, d, J=8.6 Hz), 4.99-4.93 (1H, m), 4.64-4.58 (1H, m), 4.44-4.39 (1H, m), 4.32-4.27 (1H, m), 4.24-4.20 (1H, m), 4.15-4.09 (1H, m), 3.89 (2H, s), 2.60 (2H, t, J=8.3 Hz), 2.34-2.26 (1H, m), 2.18-2.12 (1H, m), 2.02-1.98 (1H, m), 1.91-1.85 (1H, m), 1.82-1.75 (1H, m), 1.56-1.51 (18H, m), 1.34 (3H, s), 1.26 (3H, s), 1.11-1.07 (2H, m), 1.00 (1H, d, J=10.9 Hz), 0.81 (3H, s).

Reference Example 43-2: Tert-butyl 6-{[1-(azidoacetyl)azetidin-3-yl]oxy}-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Sodium azide (69.0 mg, 1.06 mmol) was added to a DMSO (4.3 mL) solution of the compound of Reference Example 43-1 (140 mg, 0.216 mmol), and the reaction mixture was stirred for 1.5 hours at room temperature. Subsequently, water was added to the reaction solution, which was diluted with ethyl acetate, and the organic phase was separated. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1/1) to obtain the title compound (129 mg).

¹H-NMR (CDCl₃) δ: 7.25-7.21 (1H, m), 6.41 (1H, d, J=8.6 Hz), 5.01-4.93 (1H, m), 4.55-4.48 (1H, m), 4.48-4.40 (1H, m), 4.27-4.19 (2H, m), 4.17-4.11 (1H, m), 3.84-3.72 (2H, m), 2.61 (2H, t, J=8.3 Hz), 2.36-2.28 (1H, m), 2.20-2.13 (1H, m), 2.04-1.99 (1H, m), 1.92-1.86 (1H, m), 1.83-1.77 (1H, m), 1.59-1.51 (18H, m), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.09 (2H, m), 1.04-0.99 (1H, m), 0.83 (3H, s).

Reference Example 43: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

2-propyn-1-ol (47 μL, 0.788 mmol), copper iodide (24.4 mg, 0.128 mmol), and tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (24.3 mg, 46.0 μmol) were added to an acetonitrile (9.2 mL) solution of the compound of Reference Example 43-2 (300 mg, 0.458 mmol), and the reaction mixture was stirred for 2 hours at room temperature. Subsequently, a saturated aqueous potassium sodium tartrate solution was added to the reaction solution, and the mixture was extracted with chloroform. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=50/1 to 30/1) to obtain the title compound (271 mg).

¹H-NMR (CDCl₃) δ: 7.75 (1H, s), 7.23 (1H, d, J=8.6 Hz), 6.40 (1H, d, J=8.6 Hz), 5.13-5.05 (1H, m), 5.02-4.93 (2H, m), 4.81 (2H, s), 4.56-4.50 (1H, m), 4.47-4.38 (1H, m), 4.27-4.22 (1H, m), 4.21-4.09 (2H, m), 2.66-2.59 (2H, m), 2.38-2.28 (2H, m), 2.22-2.14 (1H, m), 2.05-1.99 (1H, m), 1.93-1.87 (1H, m), 1.84-1.77 (1H, m), 1.57 (9H, s), 1.54 (9H, s), 1.36 (3H, d, J=1.1 Hz), 1.28 (3H, s), 1.14-1.08 (2H, m), 1.06-1.01 (1H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=711.42/3.75 min^(D)

Reference Example 44: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

The compound of Reference Example 43-2 (74.9 mg, 0.114 mmol) and (chloro[(1,2,3,4,5-h)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]bis(triphenylphosphine)ruthenium(II) (900 μg, 1.14 μmol) were added to a toluene (0.91 mL) solution of 2-propyn-1-ol (11.0 μL, 0.182 mmol), and the reaction mixture was stirred for 19 hours at 80° C. Subsequently, the reaction solution was cooled to room temperature, and stirred again for 4 hours at 80° C. after adding 2-propyn-1-ol (11.0 μL, 0.182 mmol) and chloro[(1,2,3,4,5-h)-1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]bis(triphenylphosphine)ruthenium(II) (900 μg, 1.14 μmol). Subsequently, the reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1/1 to chloroform/methanol=10/1) to obtain the title compound (45.3 mg).

¹H-NMR (CDCl₃) δ: 7.62 (1H, s), 7.22 (1H, d, J=8.6 Hz), 6.41 (1H, d, J=8.6 Hz), 5.14-5.08 (1H, m), 5.02-4.93 (2H, m), 4.71-4.62 (3H, m), 4.42-4.36 (1H, m), 4.29-4.19 (3H, m), 2.60 (2H, t, J=8.3 Hz), 2.36-2.26 (1H, m), 2.20-2.13 (1H, m), 2.03-1.99 (1H, m), 1.92-1.76 (3H, m), 1.56 (9H, s), 1.52 (9H, s), 1.35 (3H, s), 1.27 (3H, s), 1.13-1.07 (2H, m), 1.04-0.99 (1H, m), 0.82 (3H, s).

LCMS: [M+H]⁺/Rt=711.60/3.75 min^(D)

Reference Example 45: Tert-butyl 6-({1-[(5-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 43-2 as the starting material by the same method described in Reference Example 44 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 7.59 (1H, s), 7.21 (1H, d, J=8.6 Hz), 6.38 (1H, d, J=8.6 Hz), 5.23-5.07 (2H, m), 5.01-4.90 (1H, m), 4.62-4.36 (4H, m), 4.29-4.19 (2H, m), 4.13-4.05 (1H, m), 2.82 (3H, s), 2.59 (2H, t, J=8.3 Hz), 2.34-2.26 (1H, m), 2.20-2.11 (1H, m), 2.04-1.96 (1H, m), 1.91-1.85 (1H, m), 1.82-1.75 (1H, m), 1.57-1.51 (18H, m), 1.43 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.12-1.07 (2H, m), 1.01 (1H, d, J=10.9 Hz), 0.81 (3H, s).

LCMS: [M+H]⁺/Rt=824.80/4.16 min^(D)

Reference Example 46: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-{[4-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 46-1: Benzyl [4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetate

Water (12 mL) was added to a tert-butyl alcohol (12 mL) solution of benzyl 2-azidoacetate (2.50 g, 13.0 mmol). Sodium L-ascorbate (527 mg, 2.66 mmol), 3-butyn-1-ol (1.5 mL, 19.8 mmol), and copper sulfate pentahydrate (347 mg, 1.39 mmol) were added, and the reaction mixture was stirred for 2 hours at room temperature. Subsequently, water was added to the reaction solution, which was extracted with chloroform. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: chloroform/methanol=100/1 to 30/1) to obtain the title compound (3.13 g).

¹H-NMR (CDCl₃) δ: 7.52-7.50 (1H, m), 7.38-7.31 (5H, m), 5.21 (2H, s), 5.16 (2H, s), 3.95 (2H, q, J=6.1 Hz), 2.96 (2H, t, J=5.4 Hz).

LCMS: [M+H]⁺/Rt=262.09/1.88 min^(D)

Reference Example 46-2: {1-[2-(benzyloxy)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}acetic Acid

An aqueous 0.67M sodium dihydrogen phosphate solution (28 mL) was added to an acetonitrile (28 mL) solution of the compound of Reference Example 46-1 (1.02 g, 3.90 mmol). 2,2,6,6-tetramethylpiperidine-1-oxyl (56.3 mg, 0.360 mmol), aqueous 5% hypochlorous acid solution (2.1 mL), and aqueous 80% chlorous acid solution (0.88 mL, 7.81 mmol) were added, and the reaction mixture was stirred for 23 hours at room temperature. Subsequently, an aqueous sodium thiosulfate solution was added to the reaction solution, which was then extracted with ethyl acetate. 1M hydrochloric acid was added to the aqueous layer, which was again extracted with chloroform. The organic phase was washed with saturated saline and 1M hydrochloric acid, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure to obtain the title compound (676 mg).

¹H-NMR (CDCl₃) δ: 7.73 (1H, s), 7.37-7.31 (5H, m), 5.21 (2H, s), 5.18 (2H, s), 3.90 (2H, s).

Reference Example 46-3: Benzyl tert-butyl 2,2′-(1H-1,2,3-triazol-1,4-diyl)diacetate

Under a nitrogen atmosphere, a THE (15 mL) solution of the compound of Reference Example 46-2 (676 mg, 2.46 mmol) was cooled with ice. tert-butyl alcohol (10 mL) and N,N′-diisopropyl-O-t-butylisourea (1.8 mL, 0.789 mmol) were added, and the reaction mixture was stirred for 17 hours at room temperature. The reaction solution was evaporated under reduced pressure, and then the resulting residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=2/1) to obtain the title compound (425 mg).

¹H-NMR (CDCl₃) δ: 7.72 (1H, s), 7.39-7.31 (5H, m), 5.21 (2H, s), 5.16 (2H, s), 3.75 (2H, s), 1.45 (9H, s).

Reference Example 46-4: [4-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-1-yl]acetic Acid

10% palladium on carbon (88.7 mg) was added to an ethyl acetate (12 mL) solution of the compound of Reference Example 46-3 (397 mg, 1.20 mmol). Under a hydrogen atmosphere, the reaction mixture was stirred for 50 minutes at room temperature. Subsequently, the reaction solution was filtered through celite and then the filtrate was evaporated under reduced pressure to obtain the title compound (288 mg).

¹H-NMR (CD₃OD) δ: 7.91 (1H, s), 5.19 (2H, s), 3.70 (2H, s), 1.45 (9H, s).

Reference Example 46: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-{[4-(2-tert-butoxy-2-oxoethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

The compound of Reference Example 1-8 (503 mg, 0.828 mmol), triethylamine (0.350 mL, 2.51 mmol), 1-hydroxybenzotriazole (231 mg, 1.71 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (237 mg, 1.71 mmol) were added to a DMF solution (8.3 mL) of the compound of Reference Example 46-4 (277 mg, 1.15 mmol) while cooling with ice. After stirring for 1.5 hours at room temperature, water was added to the reaction solution, which was then extracted with a hexane/ethyl acetate (1:1) mixture solution. The organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution, 1 N hydrochloric acid, and saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1/2 to 1/3) to obtain the title compound (394 mg).

¹H-NMR (CDCl₃) δ: 7.78 (1H, s), 7.22 (1H, d, J=8.6 Hz), 6.38 (1H, d, J=8.6 Hz), 5.10-4.90 (3H, m), 4.50-4.38 (2H, m), 4.27-4.10 (3H, m), 3.76 (2H, s), 2.61 (2H, t, J=8.3 Hz), 2.36-2.28 (1H, m), 2.21-2.14 (1H, m), 2.06-2.00 (1H, m), 1.92-1.87 (1H, m), 1.84-1.76 (1H, m), 1.56 (9H, s), 1.54 (9H, s), 1.46 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.08 (2H, m), 1.03 (1H, d, J=10.9 Hz), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=795.55/4.19 min^(D)

Reference Example 47: [4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1H-1,2,3-triazol-1-yl]acetic Acid

Reference Example 47-1: Tert-butyl 6-{[1-({1-[2-(benzyloxy)-2-oxoethyl]-1H-1,2,3-triazol-4-yl}acetyl)azetidin-3-yl]oxy}-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 36-4 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 7.77 (1H, s), 7.39-7.31 (5H, m), 7.22 (1H, d, J=8.6 Hz), 6.40 (1H, d, J=8.6 Hz), 5.22 (2H, s), 5.18 (2H, d, J=1.7 Hz), 4.96-4.89 (1H, m), 4.66-4.61 (1H, m), 4.40-4.34 (1H, m), 4.29-4.22 (2H, m), 4.11-4.05 (1H, m), 3.72-3.58 (2H, m), 2.64-2.58 (2H, m), 2.36-2.28 (1H, m), 2.20-2.14 (1H, m), 2.04-2.00 (1H, m), 1.92-1.87 (1H, m), 1.83-1.77 (1H, m), 1.59-1.52 (18H, m), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.09 (2H, m), 1.03 (1H, d, J=10.9 Hz), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=829.46/4.22 min^(D)

Reference Example 47: [4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1H-1,2,3-triazol-1-yl]acetic Acid

A suspension of 10% palladium on carbon (67.9 mg) in ethyl acetate was added to a methanol (4.1 mL) solution of the compound of Reference Example 47-1 (340 mg, 0.410 mmol). Subsequently, under a hydrogen atmosphere, the reaction mixture was stirred for 2 hours at room temperature. The reaction solution was filtered through celite, and the filtrate was evaporated under reduced pressure to obtain the title compound (271 mg).

¹H-NMR (CDCl₃) δ: 7.78 (1H, s), 7.21 (1H, d, J=8.6 Hz), 6.39 (1H, d, J=8.0 Hz), 5.17-4.99 (2H, m), 4.98-4.88 (1H, m), 4.61-4.55 (1H, m), 4.41-4.31 (1H, m), 4.27-4.22 (1H, m), 4.14-4.01 (2H, m), 3.70-3.62 (2H, m), 2.60 (2H, t, J=8.3 Hz), 2.37-2.13 (2H, m), 2.04-1.99 (1H, m), 1.92-1.86 (1H, m), 1.83-1.77 (1H, m), 1.55 (9H, s), 1.53 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.10 (2H, t, J=8.3 Hz), 1.03 (1H, d, J=10.9 Hz), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=739.28/3.84 min^(D)

Reference Example 48: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino] [1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 48-1: Methyl [(tert-butoxycarbonyl)amino](1H-imidazol-4-yl)acetate

Sodium hydrogen carbonate (1.03 g, 12.2 mmol) and di-tert-butyl dicarbonate (2.06 mL, 8.95 mmol) were added to a THE-water (3:1) mixture solution (18 mL) of the compound of Reference Example 39-1 (928 mg, 4.07 mmol). The reaction mixture was stirred for 20 hours at room temperature and then stirred for 2 days at 70° C. After allowing the reaction solution to cool, water (10 mL) was added, and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol) to obtain the title compound (368 mg) as a light yellow solid.

¹H-NMR (CDCl₃) δ: 7.60 (1H, s), 7.06 (1H, s), 5.74 (1H, br), 5.40 (1H, d, J=8.1 Hz), 3.76 (3H, s), 1.45 (9H, s).

LCMS: [M+H]⁺/Rt=256.2/0.93 min^(B)

Reference Example 48-2: Methyl [(tert-butoxycarbonyl)amino][1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-4-yl]acetate

Sodium hydride (23.4 mg, 60% dispersion in liquid paraffin, 0.586 mmol) was added to a DMF solution (2.1 mL) of the compound of Reference Example 48-1 (136 mg, 0.533 mmol) under a nitrogen atmosphere at 0° C., and the reaction mixture was stirred for 30 minutes at room temperature. tert-butyl bromoacetate (86.0 μL, 0.586 mmol) was added, and the reaction mixture was stirred for 3 hours. Methanol (0.1 mL) and then saturated saline (20 mL) were added to the reaction solution, which was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate) to obtain the title compound (155 mg) as a light yellow solid.

¹H-NMR (CDCl₃) δ: 7.43 (1H, s), 6.98 (1H, s), 5.76 (1H, d, J=8.1 Hz), 5.34 (1H, d, J=8.1 Hz), 4.55 (2H, s), 3.75 (3H, s), 1.47 (9H, s), 1.40 (9H, s).

LCMS: [M+H]⁺/Rt=370.7/1.59 min^(B)

Reference Example 48-3: [(tert-butoxycarbonyl)amino][1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-4-yl]acetic Acid

Triethylamine (0.291 mL, 2.10 mmol) was added to an aqueous solution (4.2 mL) of the compound of Reference Example 48-2 (155 mg, 0.420 mmol), and the reaction mixture was stirred for 1 hour. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol) to obtain the title compound (84.9 mg) as a colorless solid.

¹H-NMR (CDCl₃) δ: 7.82 (1H, s), 7.01 (1H, s), 5.97 (1H, s), 5.30 (1H, s), 4.62 (2H, s), 1.48 (9H, s), 1.44 (9H, s).

LCMS: [M+H]⁺/Rt=356.2/1.35 min^(B)

Reference Example 48: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino][1-(2-tert-butoxy-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3 mL) of the compound of Reference Example 1-7 (200 mg, 0.283 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in DMF (3 mL). Reference Example 48-3 (131 mg, 0.368 mmol), HATU (129 mg, 0.340 mmol), and triethylamine (0.118 mL, 0.850 mmol) were added, and the reaction mixture was stirred for 30 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated, and the resulting residue was purified by silica gel column chromatography (eluent:hexane/ethyl acetate) to obtain the title compound (208 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.42 (1H, d, J=2.7 Hz), 7.20 (1H, dd, J=8.1 Hz, 5.4 Hz), 6.97 (1H, d, J=5.4 Hz), 6.36 (1H, d, J=5.4 Hz), 5.86-5.71 (1H, m), 5.26 (1H, d, J=8.1 Hz), 4.98-4.82 (1H, m), 4.76-4.05 (7H, m) 2.63-2.57 (2H, m), 2.36-2.27 (1H, m), 2.20-2.13 (1H, m) 2.04-2.00 (1H, m) 1.92-1.77 (2H, m), 1.61 (9H, s), 1.53 (9H, s), 1.48-1.42 (18H, m), 1.36 (3H, s), 1.26 (3H, s), 1.13-1.01 (3H, m), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=910.2/2.97 min^(B)

Reference Example 49: Tert-butyl 6-[(1-{[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl][(tert-butoxycarbonyl)amino]acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 49-1: Methyl [1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl][(tert-butoxycarbonyl)amino]acetate

Sodium hydroxide (70.5 mg, 60% dispersion in liquid paraffin, 1.76 mmol) was added to a DMF solution (6.4 mL) of the compound of Reference Example 48-1 (409 mg, 1.60 mmol) under a nitrogen atmosphere at 0° C., and the reaction mixture was stirred for 30 minutes at room temperature. 2-bromoacetamide (243 mg, 1.76 mmol) was added, and the reaction mixture was stirred for 1.5 hours. Methanol (0.1 mL) was added to the reaction solution, and the mixture was purified by silica gel column chromatography (eluent: methylene chloride/methanol) to obtain a mixture (564 mg) of the title compound and a regioisomer thereof. The resulting mixture was further purified by silica gel column chromatography (amine silica gel, eluent: ethyl acetate/methanol). The resulting mixture (396 mg) of the title compound and a regioisomer thereof was triturated in methylene chloride, filtered, and dried and solidified under reduced pressure to obtain the title compound (198 mg) as a colorless solid.

¹H-NMR (DMSO-d₆) δ: 7.51 (1H, s), 7.47-7.19 (3H, m), 7.10 (1H, s), 5.19 (1H, d, J=8.1 Hz), 4.59 (2H, s), 3.62 (3H, s), 1.39 (9H, s).

LCMS: [M+H]⁺/Rt=313.2/0.66 min^(B)

Reference Example 49-2: [1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl][(tert-butoxycarbonyl)amino]acetic acid.½(triethylamine) Salt

Triethylamine (0.204 mL, 1.47 mmol) was added to an aqueous solution (3.0 mL) of the compound of Reference Example 49-1 (92.0 mg, 0.295 mmol), and the reaction mixture was stirred for 30 minutes. The reaction solution was concentrated under reduced pressure to obtain the title compound (123 mg) as a colorless amorphous compound.

¹H-NMR (CD₃OD) δ: 7.69 (1H, s), 7.08 (1H, s), 5.03 (1H, s), 4.72 (2H, s), 3.62 (3H, s), 3.18 (3H, q, J=8.1 Hz), 1.42 (9H, s), 1.29 (4.5H, t, J=8.1 Hz).

LCMS: [M+H]⁺/Rt=299.4/0.50 min^(B)

Reference Example 49: Tert-butyl 6-[(1-{[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl][(tert-butoxycarbonyl)amino]acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 (200 mg, 0.283 mmol) and the compound of Reference Example 49-2 (109 mg, 0.312 mmol) as the starting materials by the same method described in Reference Example 42 to obtain the title compound (130 mg) as a colorless solid.

¹H-NMR (CDCl₃) δ: 7.46 (1H, s), 7.21 (1H, dd, J=8.1 Hz, 5.4 Hz), 6.97-6.95 (1H, m), 6.41-6.37 (1H, m), 5.88-5.59 (3H, m), 5.25-5.22 (1H, m), 5.00-4.87 (1H, m), 4.83-4.57 (3H, m), 4.48-4.33 (1H, m), 4.27-4.23 (1H, m), 4.16-4.05 (2H, m), 2.63-2.57 (2H, m), 2.36-2.27 (1H, m), 2.19-2.13 (1H, m), 2.04-2.00 (1H, m), 1.92-1.77 (2H, m), 1.62-1.53 (18H, m), 1.43 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.13-1.00 (3H, m), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=853.0/2.49 min^(B)

Reference Example 50: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](1H-1,2,3-triazol-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 50-1: Ethyl (1-benzyl-1H-1,2,3-triazol-4-yl)(hydroxy)acetate

After adding benzylazide (0.10 mL), copper iodide (44.6 mg, 0.234 mmol), and tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (41.4 mg, 78.0 μmol) to an acetonitrile (7.8 mL) solution of ethyl 2-hydroxy-3-butynoate (91 μL, 0.780 mmol) and stirring the reaction mixture for 5 hours at room temperature, a saturated aqueous potassium sodium tartrate solution was added to the reaction solution, and the mixture was extracted with chloroform. The organic phase was washed with saturated saline, and then dried over anhydrous sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=1/2) to obtain the title compound (187 mg).

¹H-NMR (CDCl₃) δ: 7.45 (1H, s), 7.38-7.33 (3H, m), 7.27-7.23 (2H, m), 5.50 (2H, s), 5.34 (1H, d, J=5.7 Hz), 4.33-4.18 (2H, m), 3.44 (1H, d, J=6.3 Hz), 1.24 (3H, t, J=7.2 Hz).

Reference Example 50-2: Ethyl (1-benzyl-1H-1,2,3-triazol-4-yl)[(methanesulfonyl)oxy]acetate

Under a nitrogen atmosphere, triethylamine (0.12 mL, 0.856 mmol) and methanesulfonyl chloride (36 μL, 0.476 mmol) were added to a dichloromethane (1.9 mL) solution of the compound of Reference Example 50-1 (102 mg, 0.389 mmol), and the reaction mixture was stirred for 4 hours at 0° C. Subsequently, a saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure to obtain the title compound (110 mg).

¹H-NMR (CDCl₃) δ: 7.59 (1H, s), 7.39-7.36 (3H, m), 7.28-7.25 (2H, m), 6.16 (1H, s), 5.57-5.47 (2H, m), 4.33-4.22 (2H, m), 3.14 (3H, s), 1.27-1.24 (3H, m).

Reference Example 50-3: Ethyl azide(1-benzyl-1H-1,2,3-triazol-4-yl)acetate

Under a nitrogen atmosphere, a DMF (4.0 mL) solution of the compound of Reference Example 50-2 (156 mg, 0.406 mmol) was cooled with ice. Sodium azide (39.6 mg, 0.609 mmol) was added, and the reaction mixture was stirred for 3.5 hours while cooling with ice. Subsequently, a saturated sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1) to obtain the title compound (88.7 mg).

¹H-NMR (CDCl₃) δ: 7.56 (1H, s), 7.40-7.37 (3H, m), 7.29-7.26 (2H, m), 5.55 (2H, s), 5.14 (1H, s), 4.34-4.19 (2H, m), 1.30-1.25 (3H, m).

Reference Example 50-4: Ethyl [(tert-butoxycarbonyl)amino](1H-1,2,3-triazol-4-yl)acetate

The compound of Reference Example 50-3 (101 mg, 0.349 mmol) and di-tert-butyl dicarbonate (114 mg, 0.524 mmol) were added to an ethanol (12 mL) solution of 10% palladium on carbon (10.4 mg), and then, under a hydrogen atmosphere, the reaction mixture was stirred for 2 hours at room temperature. Subsequently, 1M hydrochloric acid (0.35 mL) was added to the reaction solution, and the reaction mixture was further stirred for 44 hours at room temperature. The reaction solution was filtered through celite, and the filtrate was evaporated under reduced pressure to obtain the title compound (98.9 mg).

¹H-NMR (CDCl₃) δ: 7.74 (1H, s), 5.81-5.49 (2H, m), 4.34-4.09 (2H, m), 1.44 (9H, s), 1.27-1.21 (3H, m).

Reference Example 50-5: [(tert-butoxycarbonyl)amino](1H-1,2,3-triazol-4-yl)acetic Acid

Lithium hydroxide monohydrate (14.1 mg, 0.336 mmol) was added to a THF/water (3:1) mixture solution (1.7 mL) of the compound of Reference Example 50-4 (45.4 mg, 0.168 mmol), and the reaction mixture was stirred for 3 hours at room temperature. Subsequently, 1M hydrochloric acid was added until the pH was 4, and the mixture was extracted with ethyl acetate, and then the aqueous layer was extracted again with chloroform. The organic phase was washed with saturated saline, and then dried over sodium sulfate and filtered, then the filtrate was evaporated under reduced pressure. The resulting residue was washed and purified by decantation with diethyl ether to obtain the title compound (12.7 mg).

¹H-NMR (CD₃OD) δ: 7.93-7.65 (1H, m), 5.51-5.32 (1H, m), 1.45 (9H, s).

Reference Example 50: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](1H-1,2,3-triazol-4-yl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 and the compound of Reference Example 50-5 as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 7.71-7.62 (1H, m), 7.24-7.17 (1H, m), 6.39-6.32 (1H, m), 5.96-5.78 (1H, m), 5.52-5.37 (1H, m), 5.04-4.84 (1H, m), 4.62-3.93 (5H, m), 2.67-2.58 (2H, m), 2.51-2.27 (1H, m), 2.25-2.12 (1H, m), 2.04-1.99 (1H, m), 1.95-1.86 (1H, m), 1.83-1.74 (1H, m), 1.66-1.26 (33H, m), 1.14-1.08 (2H, m), 1.04-0.99 (1H, m), 0.83 (3H, s).

LCMS: [M+H]⁺/Rt=796.42/2.30 min^(D)

Reference Example 51: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 51-1: Tert-butyl (4-nitro-1H-1,2,3-triazol-1-yl)acetate

1-(dimethylamino)-2-nitroethylene (1.57 g, 13.5 mmol) was added to a 1,4-dioxane (8.2 mL) solution of tert-butyl 2-azidoacetate (1.29 g, 8.21 mmol), and the reaction mixture was stirred for 12 hours under microwave irradiation at 120° C. Subsequently, the reaction solution was evaporated under reduced pressure to obtain the title compound (226 mg).

¹H-NMR (CDCl₃) δ: 8.45 (1H, s), 5.13 (2H, s), 1.50 (9H, s)

LCMS: [M+H]⁺/Rt=229.13/2.48 min^(D)

Reference Example 51-2: (4-nitro-1H-1,2,3-triazol-1-yl)acetic Acid

A 4 N hydrogen chloride-1,4-dioxane solution (14 mL) was added to the compound of Reference Example 51-1 (329 mg, 1.44 mmol), and the reaction mixture was stirred for 23 hours at room temperature. Subsequently, the reaction solution was evaporated under reduced pressure to obtain the title compound.

¹H-NMR (CD₃OD) δ: 8.94 (1H, s), 5.35-5.30 (2H, m).

Reference Example 51: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 and the compound of Reference Example 51-2 as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 8.57 (1H, s), 6.43 (1H, d, J=8.6 Hz), 5.16-4.98 (3H, m), 4.65-4.57 (1H, m), 4.48-4.41 (1H, m), 4.36-4.29 (1H, m), 4.26-4.21 (1H, m), 4.20-4.13 (1H, m), 2.66-2.56 (2H, m), 2.33-2.28 (1H, m), 2.18-2.13 (1H, m), 2.05-1.97 (1H, m), 1.91-1.85 (1H, m), 1.82-1.75 (2H, m), 1.55 (9H, s), 1.52 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.12-1.07 (2H, m), 1.03-0.98 (1H, m), 0.82 (3H, s).

Reference Example 52: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-D-serylazetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 52-1: Tert-butyl 6-[(1-{N-[(benzyloxy)carbonyl]-D-seryl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (114.4 mg, 0.188 mmol) and N-carbobenzoxy-D-serine (91.8 mg, 0.384 mmol) as the starting materials by the same method described in Reference Example 3 to obtain the title compound (71.4 mg).

¹H-NMR (CD₃OD) δ: 7.39-7.26 (6H, m), 6.67 (1H, d, J=8.5 Hz), 5.12-5.05 (3H, m), 4.39-4.33 (1H, m), 4.29 (2H, d, J=8.5 Hz), 4.00-3.94 (1H, m), 3.74-3.67 (2H, m), 3.34 (2H, s), 2.58 (2H, t, J=7.9 Hz), 2.39-2.32 (1H, m), 2.21-2.16 (1H, m), 1.99 (1H, t, J=5.5 Hz), 1.89-1.87 (1H, m), 1.79 (1H, d, J=15.3 Hz), 1.55 (9H, d, J=7.9 Hz), 1.52 (9H, s), 1.35 (3H, s), 1.29 (3H, s), 1.08 (2H, t, J=8.2 Hz), 0.99 (1H, d, J=10.4 Hz), 0.86 (3H, s).

LCMS: [M+H]⁺/Rt=793.48/1.381 min^(A)

Reference Example 52: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[(1-D-serylazetidin-3-yl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3.0 mL) of the compound of Reference Example 52-1 (200 mg, 0.252 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated to obtain the title compound (198 mg).

¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J=8.1 Hz), 6.44-6.40 (1H, m), 5.01-4.94 (1H, m), 4.71-4.06 (5H, m), 3.74-3.49 (3H, m), 2.64-2.58 (2H, m), 2.45-2.00 (6H, m), 1.93-1.77 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=659.7/2.31 min^(B)

Reference Example 53: Tert-butyl 6-({1-[N²-(tert-butoxycarbonyl)-N-methyl-D-asparaginyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 53-1: Tert-buty 6-[(1-{(2R)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 and benzyl (R)-3-[(tert-butoxycarbonyl)amino]-4-oxobutanoate as the starting materials by the same method described in Reference Example 3 to obtain the title compound (1.84 g).

¹H-NMR (CDCl₃) δ: 7.40-7.31 (5H, m), 7.21 (1H, d, J=8.6 Hz), 6.40-6.30 (1H, m), 5.37-5.24 (1H, m), 5.16-5.07 (2H, m), 4.97-4.54 (3H, m), 4.42-4.27 (2H, m), 4.27-4.22 (1H, m), 4.08-4.00 (1H, m), 2.84-2.73 (2H, m), 2.65-2.57 (2H, m), 2.37-2.27 (1H, m), 2.24-2.13 (1H, m), 2.04-2.00 (1H, m), 1.93-1.87 (1H, m), 1.84-1.77 (1H, m), 1.56 (9H, s), 1.53 (9H, s), 1.44-1.40 (9H, m), 1.36 (3H, s), 1.28 (3H, s), 1.15-1.08 (2H, m), 1.06-1.01 (1H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=877.72/4.54 min^(D)

Reference Example 53-2: (3R)-3-[(tert-butoxycarbonyl)amino]-4-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-4-oxobutanoic Acid

A suspension of 10% palladium on carbon (150 mg) in ethyl acetate was added to an ethyl acetate (17 mL) solution of the compound of Example 53-1 (1.50 g, 1.71 mmol). Subsequently, under a hydrogen atmosphere, the reaction mixture was stirred for 3 hours at room temperature. The reaction solution was filtered through celite, and the filtrate was evaporated under reduced pressure to obtain the title compound (1.34 g).

¹H-NMR (CD₃OD) δ: 7.32 (1H, d, J=8.0 Hz), 6.69 (1H, d, J=8.6 Hz), 5.15-5.08 (1H, m), 4.63-4.59 (1H, m), 4.55-4.27 (4H, m), 3.99-3.92 (1H, m), 2.82-2.69 (1H, m), 2.61-2.51 (3H, m), 2.40-2.31 (1H, m), 2.23-2.14 (1H, m), 2.02-1.97 (2H, m), 1.92-1.86 (1H, m), 1.83-1.76 (1H, m), 1.57 (9H, s), 1.52 (9H, s), 1.47-1.40 (9H, m), 1.36 (3H, s), 1.30 (3H, s), 1.11-1.05 (2H, m), 1.02-0.96 (1H, m), 0.86 (3H, s).

LCMS: [M+H]⁺/Rt=787.62/4.14 min^(D)

Reference Example 53: Tert-butyl 6-({1-[N²-(tert-butoxycarbonyl)-N-methyl-D-asparaginyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 53-2 and methylamine hydrochloride as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (270 mg).

¹H-NMR (CD₃OD) δ: 7.32 (1H, d, J=8.6 Hz), 6.68 (1H, d, J=8.6 Hz), 5.14-5.07 (1H, m), 4.61-4.27 (5H, m), 4.00-3.91 (1H, m), 2.74-2.54 (6H, m), 2.49-2.41 (1H, m), 2.41-2.32 (1H, m), 2.23-2.14 (1H, m), 2.01-1.97 (1H, m), 1.92-1.86 (1H, m), 1.83-1.76 (1H, m), 1.57 (9H, s), 1.52 (9H, s), 1.46-1.40 (9H, m), 1.36 (3H, s), 1.30 (3H, s), 1.11-1.04 (2H, m), 1.01-0.95 (1H, m), 0.86 (3H, s).

LCMS: [M+H]⁺/Rt=800.73/4.09 min^(D)

Reference Example 54: Tert-butyl 6-({1-[N²-(tert-butoxycarbonyl)-N,N-dimethyl-D-asparaginyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 53-2 and dimethylamine hydrochloride as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (251 mg).

¹H-NMR (CDCl₃) δ: 7.18 (1H, d, J=8.6 Hz), 6.36 (1H, d, J=8.6 Hz), 5.82-5.50 (1H, m), 4.94-4.86 (1H, m), 4.85-4.72 (1H, m), 4.64-4.53 (1H, m), 4.43-4.31 (2H, m), 4.26-4.19 (1H, m), 4.08-3.99 (1H, m), 2.99-2.84 (8H, m), 2.62-2.54 (2H, m), 2.34-2.25 (1H, m), 2.18-2.12 (1H, m), 2.02-1.98 (1H, m), 1.90-1.85 (1H, m), 1.83-1.75 (1H, m), 1.54 (9H, s), 1.51 (9H, s), 1.40 (9H, s), 1.33 (3H, s), 1.26 (3H, s), 1.12-1.06 (2H, m), 1.03-0.99 (1H, m), 0.81 (3H, s).

LCMS: [M+H]⁺/Rt=814.69/4.15 min^(D)

Reference Example 55: Tert-butyl 6-{[(3R)-1-{[(tert-butoxycarbonyl)amino](1H-imidazol-4-yl)acetyl}pyrrolidin-3-yl]oxy}-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Reference Example 55-1: Benzyl (3R)-3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]pyrrolidine-1-carboxylate

Cyanomethylenetri-n-butylphosphorane (0.762 mL, 2.90 mmol) was added dropwise to a toluene solution (5 mL) of the compound of Reference Example 1-6 (500 mg, 0.968 mmol) and (S)-1-Cbz-3-pyrrolidinol (321 mg). The reaction solution was warmed up to 100° C., and stirred for 3 hours. The reaction solution was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=90/10 to 65/35) to obtain the title compound (681 mg).

¹H-NMR (CDCl₃) δ: 7.29-7.25 (5H, m), 7.14 (1H, dd, J=8.5, 3.0 Hz), 6.60 (1H, dd, J=12.2, 8.5 Hz), 5.08-5.03 (2H, m), 4.82 (1H, s), 4.18-4.16 (1H, m), 3.69-3.45 (4H, m), 2.55-2.53 (2H, m), 2.26-2.23 (1H, m), 2.14-2.10 (2H, m), 1.96-1.94 (2H, m), 1.84-1.81 (1H, m), 1.76-1.72 (1H, m), 1.45-1.44 (18H, m), 1.29 (3H, s), 1.21 (3H, s), 1.05-1.03 (2H, m), 0.97 (1H, d, J=10.4 Hz), 0.76 (3H, s).

Reference Example 55-2: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[(3R)-pyrrolidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

10% palladium on carbon (340 mg) was added to a methanol (5 mL) solution of the compound of Reference Example 55-1 (681 mg, 0.945 mmol), and the reaction mixture was stirred for 5 hours under a hydrogen atmosphere at room temperature. The reaction solution was filtered through celite, and the filtrate was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=95/5 to 80/20) to obtain the title compound (333 mg).

LCMS: [M+H]⁺/Rt=586/0.990 min^(A)

Reference Example 55: Tert-butyl 6-{[(3R)-1-{[(tert-butoxycarbonyl)amino](1H-imidazol-4-yl)acetyl}pyrrolidin-3-yl]oxy}-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 55-2 (86 mg, 0.138 mmol) as the starting material by the same method described in Reference Example 36-4 to obtain the title compound (90.7 mg).

LCMS: [M+H]⁺/Rt=809.53/0.874 min^(E)

Reference Example 56: Tert-butyl 4-(1-[(tert-butoxycarbonyl)amino]-2-{(3S)-3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]pyrrolidin-1-yl}-2-oxoethyl)-1H-imidazole-1-carboxylate

Reference Example 56-1: Benzyl (3S)-3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-6 and (R)-1-Cbz-3-pyrrolidinol as the starting materials by the same method described in Reference Example 55-1 to obtain the title compound.

¹H-NMR (CDCl₃) δ: 7.30-7.21 (5H, m), 7.17-7.11 (1H, m), 6.60 (1H, dd, J=12.8, 8.5 Hz), 5.10-5.01 (2H, m), 4.83-4.80 (1H, m), 4.18-4.16 (1H, m), 3.69-3.45 (4H, m), 2.55-2.53 (2H, m), 2.28-2.21 (1H, m), 2.14-2.10 (2H, m), 1.95 (2H, t, J=5.5 Hz), 1.83-1.80 (1H, m), 1.76-1.72 (1H, m), 1.45-1.44 (18H, m), 1.29 (3H, s), 1.21 (3H, s), 1.05-1.03 (2H, m), 0.97 (1H, d, J=11.0 Hz), 0.76 (3H, s).

Reference Example 56-2: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[(3S)-pyrrolidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 56-1 as the starting material by the same method described in Reference Example 55-2 to obtain the title compound.

LCMS: [M+H]⁺/Rt=586/0.993 min^(A)

Reference Example 56: Tert-butyl 4-(1-[(tert-butoxycarbonyl)amino]-2-{(3S)-3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]pyrrolidin-1-yl}-2-oxoethyl)-1H-imidazole-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 56-2 (54 mg, 0.093 mmol) and [(tert-butoxycarbonyl)amino][1-(tert-butoxycarbonyl)-1H-imidazol-4-yl]acetic acid (38 mg, 0.11 mmol) as the starting materials by the same method described in Reference Example 55 to obtain the title compound (47 mg).

LCMS: [M+H]⁺/Rt=909.53/1.356 min^(E)

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 and carboxylic acid corresponding to each of the following Reference Examples as the starting materials by the same method described in Reference Example 36-4 to obtain each of Reference Example compounds 57 to 62 shown in Tables 2-7 and 2-8.

TABLE 2-7 Reference Example Structural formula NMR and/or LCMS 57

LCMS: [M + H]⁺/Rt = 809.49/0.973 min^(C) 58

LCMS: [M + H]⁺/Rt = 707.43/1.187 min^(A) 59

LCMS: [M + H]⁺/Rt = 681.60/3.75 min^(D) ¹H-NMR (CDCl₃) δ: 7.66 (1H, s), 7.20 (1H, d, J = 8.0 Hz), 6.38 (1H, d, J = 8.6 Hz), 4.99-4.87 (1H, m), 4.55-4.49 (1H, m), 4.40- 4.34 (1H, m), 4.28-4.20 (1H, m), 4.12-4.06 (1H, m), 3.62-3.58 (2H, m), 2.63-2.54 (2H, m), 2.33-2.24 (1H, m), 2.21-2.10 (1H, m), 2.03-1.96 (1H, m), 1.90-1.84 (1H, m), 1.81- 1.74 (1H, m), 1.53-1.51 (18H, m), 1.34 (3H, s), 1.26 (3H, s), 1.11-1.07 (2H, m), 1.02- 0.98 (1H, m), 0.81 (3H, s). 60

¹H-NMR (CDCl₃) δ: 7.20 (2H, d, J = 8.5 Hz), 6.39 (1H, d, J = 8.5 Hz), 4.93-4.90 (1H, m), 4.42-4.31 (2H, m), 4.22 (1H, dd, J = 9.2, 1.8 Hz), 4.13-4.02 (2H, m), 3.59-3.55 (1H, m), 3.44-3.38 (1H, m), 3.29-3.25 (1H, m), 2.92-2.87 (1H, m), 2.59 (3H, t, J = 8.2 Hz), 2.35-2.23 (1H, m), 2.19-2.12 (3H, m), 2.09-2.02 (2H, m), 1.88-1.85 (1H, m), 1.78 (1H, d, J = 14.6 Hz), 1.54 (9H, s), 1.52 (18H, s), 1.43 (3H, s), 1.34 (3H, s), 1.09 (2H, t, J = 8.5 Hz), 1.01 (1H, d, J = 11.0 Hz), 0.82 (3H, s).

TABLE 2-8 61

¹H-NMR (CDCl₃) δ: 7.21 (1H, d, J = 8.5 Hz), 6.40 (1H, d, J = 8.5 Hz), 4.94-4.90 (1H, m), 4.70-4.30 (4H, m), 4.25 (1H, dd, J = 8.9, 2.1 Hz), 4.13-3.80 (6H, m), 3.01-2.75 (3H, m), 2.61 (2H, t, J = 8.2 Hz), 2.35- 2.28 (1H, m), 2.20-2.14 (1H, m), 2.04-2.00 (1H, m), 1.92-1.87 (1H, m), 1.83-1.78 (1H, m), 1.56 (9H, s), 1.53 (9H, s), 1.47 (18H, s), 1.36 (3H, s), 1.27 (3H, s), 1.13 (2H, dt, J = 17.5, 6.3 Hz), 1.03 (1H, d, J = 11.0 Hz), 0.84 (3H, s) 62

LCMS: [M + H]⁺/Rt = 801.41/1.463 min^(C) ¹H-NMR (CD₃OD) δ: 7.31 (1H, d, J = 8.5 Hz), 6.69 (1H, dd, J = 8.5, 2.4 Hz), 5.30 (1H, s), 5.17 (1H, s), 5.08 (1H, s), 4.61 (1H, t, J = 7.6 Hz), 4.37 (1H, dd, J = 11.3, 6.4 Hz), 4.31-4.26 (3H, m), 4.18-4.14 (1H, m), 3.94 (1H, d, J = 11.6 Hz), 3.63 (1H, s), 3.55 (1H, s), 2.58 (2H, t, J = 7.9 Hz), 2.38-2.31 (2H, m), 2.20- 2.15 (2H, m), 1.98 (1H, t, J = 5.5 Hz), 1.89-1.85 (1H, m), 1.78 (1H, d, J = 14.6 Hz), 1.58 (9H, s), 1.52 (9H, s), 1.47 (9H, s), 1.35 (3H, s), 1.29 (3H, s), 1.07 (2H, t, J = 8.2 Hz), 0.97 (1H, dd, J = 11.0, 1.8 Hz), 0.85 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 3 to obtain each of Reference Example compounds 63 to 105 shown in Tables 2-9 to 2-16.

TABLE 2-9 Refer- ence Ex- ample Structural formula NMR and/or LCMS 63

LCMS: [M + H]⁺/Rt = 807.2/2.91 min^(B) ¹H-NMR (CDCl₃) δ: 8.63-8.57 (2H, m), 7.73-7.66 (1H, m), 7.34-7.29 (1H, m), 7.20 (1H, dd, J = 8.1 Hz, 5.4 Hz), 6.34 (1H, t, J = 8.1 Hz), 6.00-5.83 (1H, m), 5.24-5.17 (1H, m), 4.98-4.78 (1H, m), 4.64-4.42 (1H, m), 4.33-4.06 (3H, m), 4.04-3.82 (1H, m), 2.64- 2.56 (2H, m), 2.36-2.27 (1H, m), 2.21-2.12 (1H, m), 2.05-2.00 (1H, m), 1.91-1.77 (2H, m), 1.56-1.40 (27H, m), 1.36 (3H, s), 1.26 (3H, s), 1.13-1.00 (3H, m), 0.83 (3H, s). 64

LCMS: [M + H]⁺/Rt = 810.0/2.93 min^(B) ¹H-NMR (CDCl₃) δ: 7.46-7.36 (2H, m), 7.22-7.18 (1H, m), 6.36-6.33 (1H, m), 5.67-5.50 (1H, m), 5.19- 5.15 (1H, m), 5.05-4.93 (1H, m), 4.85-4.63 (1H, m), 4.48-4.22 (3H, m), 4.16-3.95 (1H, m), 3.88-3.66 (3H, m), 2.63-2.57 (2H, m), 2.36-2.27 (1H, m), 2.19- 2.14 (1H, m), 2.05-2.00 (1H, m), 1.93-1.76 (2H, m), 1.56-1.41 (27H, m), 1.35 (3H, s), 1.28 (3H, s), 1.13- 1.00 (3H, m), 0.83 (3H, s). 65

LCMS: [M + H]⁺/Rt = 813.0/2.97 min^(B) ¹H-NMR (CDCl₃) δ: 8.15 (1H, br), 7.21 (1H, d, J = 8.1 Hz), 6.71 (1H, s), 6.41 (1H, d, J = 8.1 Hz), 5.00- 4.88 (1H, m), 4.54-4.49 (1H, m), 4.42-4.35 (1H, m), 4.31-4.23 (2H, m), 4.14-4.08 (1H, m), 3.49 (2H, s), 2.65-2.56 (2H, m), 2.36-2.26 (1H, m), 2.19-2.12 (1H, m), 2.06-2.00 (1H, m), 1.92-1.77 (2H, m), 1.61- 1.44 (27H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.00 (3H, m), 0.83 (3H, s) 66

LCMS: [M + H]⁺/Rt = 798.8/3.05 min^(B) ¹H-NMR (CDCl₃) δ: 7.82 (1H, br), 7.72 (1H, s), 7.23 (1H, d, J = 8.1 Hz), 6.45 (1H, d, J = 8.1 Hz), 4.97- 4.84 (2H, m), 4.56-4.52 (2H, m), 4.26-4.19 (2H, m), 2.65-2.59 (2H, m), 2.36-2.28 (1H, m), 2.22-2.14 (1H, m), 2.04-2.00 (1H, m), 1.91-1.76 (2H, m), 1.60- 1.49 (27H, m), 1.36 (3H, s), 1.28 (3H, s), 1.15-1.01 (3H, m), 0.84 (3H, s). 67

LCMS: [M + H]⁺/Rt = 1017.7/3.24 min^(B) ¹H-NMR (CDCl₃) δ: 7.47-7.18 (11H, m), 6.92-6.87 (3H, m), 6.36-6.26 (1H, m), 5.86-5.69 (1H, m), 5.19-3.76 (11H, m), 2.63-2.57 (2H, m), 2.36-2.27 (1H, m), 2.18-2.13 (1H, m), 2.05-2.00 (1H, m), 1.89-1.77 (2H, m), 1.57-1.39 (27H, m), 1.35 (3H, s), 1.26 (3H, s), 1.14-1.00 (3H, m), 0.83 (3H, s).

TABLE 2-10 68

LCMS: [M + H]′/Rt = 1017.9/3.36 min^(B) ¹H-NMR (CDCl₃) δ: 7.41-7.15 (12H, m), 6.61-6.53 (2H, m), 6.24-6.11 (1H, m), 5.66-5.49 (2H, m), 5.11-5.00 (4H, m), 4.81-3.72 (5H, m), 2.64-2.54 (2H, m), 2.36-2.28 (1H, m), 2.20-2.16 (1H, m), 2.09-2.00 (1H, m), 1.89-1.78 (2H, m), 1.68-1.23 (33H, m), 1.14-1.02 (3H, m), 0.83 (3H, s). 69

LCMS: [M + H]⁺/Rt = 681.39/3.96 min^(D) ¹H-NMR (CDCl₃) δ: 7.78 (1H, d, J = 1.1 Hz), 7.73 (1H, d, J = 1.1 Hz), 7.23-7.18 (1H, m), 6.37 (1H, d, J = 8.6 Hz), 5.09 (1H, d, J = 16.0 Hz), 5.01-4.91 (2H, m), 4.53-4.45 (1H, m), 4.45-4.37 (1H, m), 4.26-4.21 (1H, m), 4.19-4.07 (2H, m), 2.63-2.56 (2H, m), 2.34-2.25 (1H, m), 2.20-2.12 (1H, m), 2.03-1.98 (1H, m), 1.92-1.85 (1H, m), 1.83-1.75 (1H, m), 1.54 (9H, s), 1.52 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.12-1.07 (2H, m), 1.01 (1H, d, J = 11.5 Hz), 0.82 (3H, s). 70

LCMS: [M + H]⁺/Rt = 824.0/2.51 min^(B) ¹H-NMR (CDCl₃) δ: 7.39 (1H, s), 7.22 (1H, d, J = 8.1 Hz), 6.90 (1H, s), 6.41 (1H, d, J = 8.1 Hz), 4.93-4.61 (3H, m), 4.41-4.35 (1H, m), 4.27-4.23 (2H, m), 4.06-4.00 (2H, m), 3.52-3.37 (4H, m), 2.64-2.56 (2H, m), 2.36-2.27 (1H, m), 2.19-2.13 (1H, m), 2.05-2.00 (1H, m), 1.93-1.66 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.44 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.00 (3H, m), 0.86 (3H, s). 71

LCMS: [M + H]⁺/Rt = 812.9/2.93 min^(B) ¹H-NMR (CDCl₃) δ: 8.77-8.76 (1H, m), 7.36-7.33 (1H, m), 7.22 (1H, d, J = 8.1 Hz), 6.39 (1H, d, J = 8.1 Hz), 5.98-5.92 (1H, m), 5.54-5.48 (1H, m), 5.01-4.87 (1H, m), 4.74-4.68 (1H, m), 4.48-4.03 (4H, m), 2.64-2.58 (2H, m), 2.36-2.27 (2H, m), 2.04-2.00 (1H, m), 1.92- 1.76 (2H, m), 1.57-1.52 (18H, m), 1.44 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.01 (3H, m), 0.83 (3H, s). 72

LCMS: [M + H]⁺/Rt = 865.61/1.332 min^(E)

TABLE 2-11 73

¹H-NMR (400 MHz, CDCl₃) δ: 7.39-7.37 (6H, m), 7.27-7.12 (10H, m), 6.49 (1H, d, J = 8.5 Hz), 5.16-5.13 (1H, m), 4.92-4.90 (1H, m), 4.83-4.79 (2H, m), 4.24-4.20 (3H, m), 4.13-4.07 (1H, m), 2.64-2.56 (4H, m), 2.35-2.26 (1H, m), 2.19-2.13 (1H, m), 2.02-1.99 (1H, m), 1.90-1.86 (1H, m), 1.81-1.77 (1H, m), 1.54 (9H, s), 1.51 (9H, s), 1.41 (9H, s), 1.34 (3H, s), 1.26 (3H, s), 1.11-1.00 (2H, m), 0.82 (3H, s). 74

LCMS: [M + H]⁺/Rt = 1045/1.347 min^(C) 75

LCMS: [M + H]⁺/Rt = 759.20/4.09 min^(D) ¹H-NMR (CDCl₃) δ: 7.22-7.17 (1H, m), 6.40-6.36 (1H, m), 5.58-5.41 (1H, m), 4.98-4.89 (1H, m), 4.76-4.53 (1H, m), 4.44-4.19 (3H, m), 4.13-4.02 (1H, m), 3.91- 3.80 (1H, m), 3.73-3.64 (1H, m), 2.62-2.55 (2H, m), 2.35-2.25 (1H, m), 2.19-2.11 (1H, m), 2.03-1.97 (1H, m), 1.92-1.84 (1H, m), 1.82-1.75 (1H, m), 1.54 (9H, s), 1.51 (9H, s), 1.44-1.40 (9H, m), 1.34 (3H, s), 1.26 (3H, s), 1.12-1.06 (2H, m), 1.03-0.99 (1H, m), 0.81 (3H, s). 76

LCMS: [M + H]⁺/Rt = 843.8/3.14 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.40 (1H, d, J = 8.1 Hz), 4.93 (1H, br), 4.79-4.67 (1H, m), 4.61- 4.48 (1H, m), 4.40-4.31 (2H, m), 4.25 (1H, dd, J = 8.1 Hz, 2.7 Hz), 4.14-4.05 (1H, m), 2.67-2.58 (4H, m), 2.36-2.27 (1H, m), 2.22-2.13 (1H, m), 2.04-2.00 (1H, m), 1.93-1.77 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.46- 1.42 (18H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 77

LCMS: [M + H]⁺/Rt = 814.7/2.89 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.77 (1H, br), 6.41 (1H, d, J = 8.1 Hz), 5.70-4.90 (2H, m), 4.75-4.04 (7H, m), 2.65-2.59 (2H, m), 2.36-2.28 (1H, m), 2.20-2.14 (1H, m), 2.04-2.00 (1H, m), 1.91-1.78 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36-1.23 (12H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

TABLE 2-12 78

LCMS: [M + H]⁺/Rt = 843.7/3.21 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.40 (1H, d, J = 8.1 Hz), 5.32-5.29 (1H, m), 5.00-4.84 (1H, m), 4.79-4.64 (1H, m), 4.59-4.48 (1H, m), 4.40-4.30 (2H, m), 4.27-4.23 (1H, m), 4.14-4.05 (1H, m), 2.67-2.56 (4H, m), 2.36-2.26 (1H, m), 2.22-2.13 (1H, m), 2.05- 2.00 (1H, m), 1.92-1.77 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45-1.40 (18H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 79

LCMS: [M + H]⁺/Rt = 785.7/1.40 min^(C) 80

LCMS: [M − Boc + H]⁺/Rt = 737.5/1.47 min^(C) 81

LCMS: [M + H]⁺/Rt = 787.7/1.40 min^(C) 82

LCMS: [M + H]⁺/Rt = 805.7/3.07 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 5.01-4.43 (3H, m), 4.37-4.30 (1H, m), 4.27-4.00 (3H, m), 3.85-3.75 (2H, m), 2.65-2.48 (4H, m), 2.36-2.27 (1H, m), 2.20-2.14 (1H, m), 2.05-2.00 (1H, m), 1.92-1.77 (2H, m), 1.59-1.45 (27H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

TABLE 2-13 83

LCMS: [M + H]′/Rt = 797.3/3.07 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 4.97-4.89 (1H, m), 4.45-4.32 (2H, m), 4.27-4.23 (1H, m), 4.16-4.05 (2H, m), 2.96-2.71 (4H, m), 2.65-2.56 (2H, m), 2.36-2.27 (1H, m), 2.22-2.13 (1H, m), 2.05-2.01 (5H, m), 1.92-1.67 (5H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 84

LCMS: [M + H]⁺/Rt = 769.8/3.03 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.43 (1H, d, J = 8.1 Hz), 4.99-4.93 (1H, m), 4.45-4.46 (1H, m), 4.40-4.34 (1H, m), 4.27-4.05 (3H, m), 3.60-3.26 (4H, m), 2.95-2.80 (1H, m), 2.65-2.59 (2H, m), 2.36-2.26 (1H, m), 2.22-2.13 (1H, m), 2.05-2.00 (3H, m), 1.90- 1.76 (2H, m), 1.57 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 85

LCMS: [M + H]⁺/Rt = 797.8/3.18 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 5.00-4.82 (1H, m), 4.48-4.08 (7H, m), 3.40-3.12 (1H, m), 2.64-2.58 (2H, m), 2.36-2.27 (1H, m), 2.22-2.13 (1H, m), 2.05-1.76 (5H, m), 1.60-1.56 (15H, m), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 86

LCMS: [M + H]⁺/Rt = 783.9/3.09 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 4.96-4.86 (1H, m), 4.37-4.00 (6H, m), 3.37-3.26 (2H, m), 2.80-2.58 (4H, m), 2.36-2.26 (1H, m), 2.20-2.13 (1H, m), 2.09-1.77 (7H, m), 1.56 (9H, s), 1.54 (9H, s), 1.46 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.83 (3H, s). 87

LCMS: [M + H]⁺/Rt = 783.8/3.22 min^(B) ¹H-NMR (CDCl₃) δ: 7.21 (1H, d, J = 8.1 Hz), 6.39-6.33 (1H, m), 4.94-4.68 (2H, m), 4.55-3.89 (7H, m), 2.64- 2.56 (2H, m), 2.36-2.27 (1H, m), 2.27-2.13 (1H, m), 2.05-2.00 (1H, m), 1.93-1.77 (2H, m), 1.70-1.23 (39H, m), 1.13-1.01 (3H, m), 0.83 (3H, s). 88

LCMS: [M + H]⁺/RT = 783.9/3.11 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.43 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.51-4.04 (8H, m), 2.85-2.56 (3H, m), 2.36-2.14 (3H, m), 2.05-2.00 (1H, m), 1.93-1.77 (3H, m), 1.74-1.44 (30H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

TABLE 2-14 89

LCMS: [M + H]′/Rt = 783.6/3.05 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.43 (1H, d, J = 8.1 Hz), 4.99-4.92 (1H, m), 4.51-4.45 (1H, m), 4.39-4.32 (1H, m), 4.27-4.04 (5H, m), 2.80-2.53 (3H, m), 2.36-2.25 (2H, m), 2.20-2.13 (1H, m), 2.05-2.00 (1H, m), 1.92-1.77 (2H, m), 1.71-1.51 (23H, m), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 90

LCMS: [M + H]⁺/Rt = 670.7/2.88 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 4.97-4.90 (1H, m), 4.76-4.63 (1H, m), 4.47-4.22 (4H, m), 4.14-4.05 (1H, m), 3.92-3.81 (2H, m), 2.64-2.58 (2H, m), 2.36-2.27 (1H, m), 2.21-2.11 (3H, m), 2.05-2.00 (1H, m), 1.95-1.79 (4H, m), 1.62- 1.54 (18H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 91

LCMS: [M + H]⁺/Rt = 845.8/3.14 min^(B) ¹H-NMR (CDCl₃) δ: 7.32-7.20 (6H, m), 6.42 (1H, d, J = 8.1 Hz), 5.05-4.86 (1H, m), 4.64-3.91 (7H, m), 3.49- 3.26 (2H, m), 2.64-2.58 (2H, m), 2.36-2.27 (1H, m), 2.22-2.13 (2H, m), 2.08-2.00 (2H, m), 1.96-1.78 (2H, m), 1.56-1.45 (27H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.83 (3H, s). 92

LCMS: [M + H]⁺/Rt = 781.7/3.07 min^(B) ¹H-NMR (CDCl₃) δ: 7.21 (1H, d, J = 8.1 Hz), 6.39 (1H, d, J = 8.1 Hz), 4.97-4.86 (1H, m), 4.78-4.33 (3H, m), 4.26-3.98 (3H, m), 3.50-3.42 (1H, m), 2.64-2.58 (2H, m), 2.41-2.27 (1H, m), 2.22-2.13 (1H, m), 2.05-2.00(2H, m), 1.96-1.77 (2H, m), 1.56-1.41 (29H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (4H, m), 0.96-0.69(4H, m). 93

LCMS: [M + H]⁺/Rt = 684.0/2.18 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.67-4.57 (1H, m), 4.47-4.36 (1H, m), 4.27-4.23 (2H, m), 4.15-4.05 (1H, m), 3.25-2.94 (1H, m), 2.64-2.58 (2H, m), 2.47-2.27 (5H, m), 2.21-2.14 (2H, m), 2.05-2.00 (1H, m), 1.97-1.66 (6H, m), 1.56 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 94

LCMS: [M + H]⁺/Rt = 797.9/3.23 min^(B) ¹H-NMR (CDCl₃) δ: 7.21 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 4.97-4.89 (1H, m), 4.47-4.33 (2H, m), 4.26-4.23 (1H, m), 4.16-4.03 (4H, m), 3.87-3.77 (2H, m), 2.65-2.58 (2H, m), 2.36-2.28 (1H, m), 2.21-2.12 (1H, m), 2.08-1.78 (10H, m), 1.60-1.44 (27H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

TABLE 2-15 95

LCMS: [M + H]⁺/Rt = 799.9/3.01 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 4.95-4.88 (1H, m), 4.56-4.32 (2H, m), 4.26-3.81 (6H, m), 3.57-3.48 (1H, m), 2.93-2.80 (1H, m), 2.71-2.58 (3H, m), 2.36-2.26 (2H, m), 2.22-2.10 (2H, m), 2.04-2.00 (2H, m), 1.93-1.77 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.46 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.83 (3H, s). 96

LCMS: [M + H]⁺/Rt = 769.9/2.98 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 4.98-4.91 (1H, m), 4.47-4.41 (1H, m), 4.37-4.31 (1H, m), 4.27-4.23 (1H, m), 4.18-4.02 (4H, m), 3.61-3.55 (2H, m), 2.98-2.85 (1H, m), 2.65-2.59 (2H, m), 2.42 (2H, d, J = 8.1 Hz), 2.22-2.13 (1H, m), 2.05-2.00 (1H, m), 1.92-1.76 (2H, m), 1.57 (9H, s), 1.54 (9H, s), 1.43 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 97

LCMS: [M + H]⁺/Rt = 898.9/3.14 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 5.24-5.07 (1H, m), 5.02-4.90 (1H, m), 4.55-4.00 (6H, m), 3.62-2.92 (5H, m), 2.65-2.59 (2H, m), 2.49-2.23 (2H, m), 2.22-2.12 (1H, m), 2.05-2.00 (1H, m), 1.95-1.78 (3H, m), 1.58-1.42 (36H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 98

LCMS: [M + H]⁺/Rt = 798.0/3.10 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 4.96-4.89 (1H, m), 4.49-4.32 (2H, m), 4.27-4.23 (1H, m), 4.16-4.02 (3H, m), 3.89-3.75 (1H, m), 3.33-3.26 (1H, m), 2.65-2.58 (2H, m), 2.36-2.28 (1H, m), 2.22-2.07 (3H, m), 2.05-2.00 (2H, m), 1.97-1.78 (7H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 99

LCMS: [M + H]⁺/Rt = 912.7/3.1 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 5.13-5.09 (1H, m), 5.00-4.91 (1H, m), 4.75-4.69 (1H, m), 4.54-3.99 (8H, m), 2.70-2.59 (4H, m), 2.36-2.28 (1H, m), 2.23-2.13 (1H, m), 2.05-2.00 (1H, m), 1.94-1.87 (1H, m), 1.84-1.62 (4H, m), 1.60- 1.53 (18H, m), 1.45-1.42 (18H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 100

LCMS: [M + H]⁺/Rt = 783.7/2.99 min^(B)

TABLE 2-16 101

LCMS: [M + H]⁺/Rt = 783.6/3.01 min^(B) 102

LCMS: [M + H]⁺/Rt = 783.9/3.08 min^(B) 103

LCMS: [M + H]⁺/Rt = 783.8/3.08 min^(B) 104

LCMS: [M + H]⁺/Rt = 797.9/3.17 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.42 (1H, d, J = 8.1 Hz), 4.97-4.89 (1H, m), 4.68-4.40 (2H, m), 4.36-3.94 (5H, m), 2.87-2.69 (1H, m), 2.63-2.53 (2H, m), 2.47-2.13 (4H, m), 2.04-2.00 (1H, m), 1.93-1.77 (2H, m), 1.68-1.54 (24H, m), 1.46-1.45 (9H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 105

LCMS: [M + H]⁺/Rt = 794.6/2.90 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 5.00-4.85 (1H, m), 4.61-3.92 (7H, m), 3.67-3.56 (1H, m), 3.50-2.98 (1H, m), 2.64-2.46 (3H, m), 2.41-2.13 (3H, m), 2.05-2.00 (1H, m), 1.92-1.77 (2H, m), 1.59-1.54 (18H, m), 1.45 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 as the starting material by the same method described in Reference Example 41 to obtain each of Reference Example compounds 106 to 108 shown in Table 2-17.

TABLE 2-17 Reference Example Structural formula NMR and/or LCMS 106

LCMS: [M + H]⁺/Rt = 702.8/2.72 min^(B) ¹H-NMR (CDCl₃) δ: 10.51 (1H, br), 7.62 (1H, s), 7.56 (1H, s), 7.18 (1H, d, J = 8.1 Hz), 6.30 (1H, d, J = 8.1 Hz), 4.76- 4.71 (1H, m), 4.33-4.22 (3H, m), 4.01- 3.96 (2H, m), 2.62-2.56 (2H, m), 2.36- 2.27 (1H, m), 2.19-2.13 (1H, m), 2.04- 2.00 (1H, m), 1.92-1.76 (2H, m), 1.53 (9H, s), 1.52 (9H, s), 1.35 (3H, s), 1.26 (3H, s), 1.11-1.00 (3H, m), 0.83 (3H, s). 107

LCMS: [M + H]⁺/Rt = 714.0/2.96 min^(B) ¹H-NMR (CDCl₃) δ: 9.07 (1H, d, J = 2.7 Hz), 8.88 (1H, dd, J = 5.4 Hz, 2.7 Hz), 8.15-8.11 (1H, m), 7.53 (1H, dd, J = 8.1 Hz, 5.4 Hz), 7.18 (1H, d, J = 8.1 Hz), 6.37 (1H, d, J = 8.1 Hz), 4.86-4.82 (1H, m), 4.27-4.21 (3H, m), 3.87-3.82 (2H, m), 2.62-2.56 (2H, m), 2.35-2.27 (1H, m), 2.19-2.12 (1H, m), 2.03-1.99 (1H, m), 1.91-1.76 (2H, m), 1.52 (9H, s), 1.49 (9H, s), 1.35 (3H, s), 1.26 (3H, s), 1.11- 0.99 (3H, m), 0.83 (3H, s). 108

LCMS: [M + H]⁺/Rt = 729.8/2.84 min^(B) ¹H-NMR (CDCl₃) δ: 8.23 (1H, d, J = 8.1 Hz), 7.99 (1H, dd, J = 8.1 Hz, 2.7 Hz), 7.46-7.31 (2H, m), 7.20 (1H, d, J = 8.1 Hz), 6.40 (1H, d, J = 8.1 Hz), 4.99-4.90 (1H, m), 4.60-4.54 (2H, m), 4.42-4.36 (2H, m), 4.24 (1H, dd, J = 8.1 Hz, 2.7 Hz), 2.64-2.56 (2H, m), 2.36-2.27 (1H, m), 2.22-2.13 (1H, m), 2.05-2.00 (1H, m), 1.92-1.76 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.35 (3H, s), 1.28 (3H, s), 1.13- 1.00 (3H, m), 0.83 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 as the starting material by the same method described in Reference Example 42 to obtain each of Reference Example compounds 109 to 113 shown in Table 2-18.

TABLE 2-18 Refer- ence Exam- ple Structural formula NMR and/or LCMS 109

LCMS: [M + H]⁺/Rt = 786.9/2.77 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.41-6.37 (1H, m), 6.02 (1H, br), 5.71-5.61 (1H, m), 5.48-5.39 (1H, m), 4.95-4.89 (1H, m), 4.75-4.50 (2H, m), 4.42-4.32 (2H, m), 4.27-4.23 (1H, m), 4.10-4.03 (1H, m), 2.73-2.54 (4H, m), 2.36-2.27 (1H, m), 2.20-2.13 (1H, m), 2.04-2.00 (1H, m), 1.92-1.77 (2H, m), 1.57 (9H, s), 1.53 (9H, s), 1.43 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.83 (3H, s). 110

LCMS: [M + H]⁺/Rt = 671.6/2.59 min^(B) ¹H-NMR (CDCl₃) δ: 7.32 (1H, d, J = 8.1 Hz), 6.70 (1H, d, J = 8.2 Hz), 5.12-5.06 (1H, m), 4.68-4.62 (1H, m), 4.40-4.17 (3H, m), 3.96-3.90 (1H, m), 2.60-2.49 (4H, m), 2.45-2.31 (3H, m), 2.23-2.11 (1H, m), 2.01-1.97 (1H, m), 1.90-1.66 (2H, m), 1.56 (9H, s), 1.52 (9H, s), 1.35 (3H, s), 1.29 (3H, s), 1.20-0.96 (3H, m), 0.86 (3H, s). 111

LCMS: [M + H]⁺/Rt = 800.8/2.72 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.43-6.39 (1H, m), 5.01-4.91 (1H, m), 4.69-4.02 (6H, m), 2.64-2.58 (2H, m), 2.36-1.76 (9H, m), 1.61-1.53 (18H, m), 1.43-1.42 (9H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 112

LCMS: [M + H]⁺/Rt = 800.7/2.81 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 6.23-6.16 (1H, m), 5.56-5.40 (1H, m), 5.00-4.92 (1H, m), 4.75-4.65 (1H, m), 4.56-4.23 (4H, m), 4.12-4.03 (1H, m), 3.67-3.27 (2H, m), 2.64-2.58 (2H, m), 2.37-2.27 (1H, m), 2.22-2.12 (1H, m), 2.04-1.98 (4H, m), 1.93-1.77 (2H, m), 1.60-1.54 (18H, m), 1.44 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 113

LCMS: [M + H]⁺/Rt = 801.7/2.70 min^(B) ¹H-NMR (CDCl₃) δ: 7.26-7.21 (1H, m), 6.43 (1H, d, J = 8.1 Hz), 6.25 (1H, br), 5.30-4.95 (2H, m), 4.75-4.52 (3H, m), 4.44-4.05 (5H, m), 3.74-3.15 (2H, m), 2.63-2.57 (2H, m), 2.37-2.28 (1H, m), 2.23-2.13 (1H, m), 2.05-2.01 (1H, m), 1.93-1.77 (2H, m), 1.57 (9H, s), 1.52 (9H, s), 1.44 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.01 (3H, m), 0.84 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 43-2 as the starting material by the same method described in Reference Example 43 to obtain each of Reference Example compounds 114 to 116 shown in Table 2-19.

TABLE 2-19 Refer- ence Exam- ple Structural formula NMR and/or LCMS 114

LCMS: [M + H]⁺/Rt = 824.58/4.36 min^(D) ¹H-NMR (CDCl₃) δ: 7.76-7.65 (1H, m), 7.24 (1H, d, J = 8.6 Hz), 6.41 (1H, d, J = 8.6 Hz), 5.11-5.04 (1H, m), 5.02-4.96 (1H, m), 4.95-4.89 (1H, m), 4.60-4.48 (3H, m), 4.47- 4.40 (1H, m), 4.31-4.20 (2H, m), 4.19-4.11 (1H, m), 2.92 (3H, s), 2.63 (2H, t, J = 8.3 Hz), 2.38-2.29 (1H, m), 2.23-2.14 (1H, m), 2.07- 2.01 (1H, m), 1.94-1.88 (1H, m), 1.86-1.78 (1H, m), 1.58 (9H, s), 1.55 (9H, s), 1.48 (9H, s), 1.37 (3H, s), 1.30 (3H, s), 1.13 (2H, t, J = 8.3 Hz), 1.04 (1H, d, J = 10.9 Hz), 0.85 (3H, s). 115

LCMS: [M + H]⁺/Rt = 879.59/3.24 min^(D) ¹H-NMR (CDCl₃) δ: 7.72 (1H, s), 7.40-7.17 (1H, m), 6.48-6.36 (1H, m), 5.12-4.87 (3H, m), 4.62-4.51 (1H, m), 4.49-4.36 (1H, m), 4.30- 4.21 (2H, m), 4.19-4.09 (1H, m), 3.74-3.65 (2H, m), 3.51-3.37 (4H, m), 2.67-2.56 (2H, m), 2.54-2.41 (4H, m), 2.36-2.26 (1H, m), 2.21- 2.12 (1H, m), 2.06-1.99 (1H, m), 1.94-1.75 (2H, m), 1.62-1.42 (27H, m), 1.38-1.35 (3H, m), 1.30-1.27 (3H, m), 1.14-1.08 (2H, m), 1.06-1.00 (1H, m), 0.86-0.82 (3H, m). 116

LCMS: [M + H]⁺/Rt = 725.50/3.77 min^(D) ¹H-NMR (CDCl₃) δ: 7.62 (1H, s), 7.22 (1H, d, J = 8.6 Hz), 6.38 (1H, d, J = 8.6 Hz), 5.10-4.90 (3H, m), 4.53-4.39 (2H, m), 4.28-4.22 (1H, m), 4.16-4.04 (2H, m), 3.98-3.82 (2H, m), 2.96 (2H, t, J = 5.7 Hz), 2.65-2.56 (3H, m), 2.37-2.26 (1H, m), 2.21-2.12 (1H, m), 2.04-2.00 (1H, m), 1.94-1.88 (1H, m), 1.86- 1.74 (1H, m), 1.57 (9H, s), 1.54 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.13-1.08 (2H, m), 1.03 (1H, d, J = 10.9 Hz), 0.84 (3H, s).

Reference Example 117: Tert-butyl (4R)-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}-4-hydroxypyrrolidine-1-carboxylate

Palladium on carbon (20 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3 mL) of the compound of Reference Example 1-7 (200 mg, 0.283 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methanol, and the combined filtrate was concentrated. The resulting residue was dissolved in DMF (2 mL) (this is referred to as “solution A”)t. Meanwhile, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (94.1 mg, 0.340 mmol) was added to a DMF-methanol (2:1) mixture solution (3 mL) of trans-N-(tert-butoxycarbonyl)-4-hydroxy-L-proline (98.3 mg, 0.425 mmol), and the reaction mixture was stirred for 20 minutes at room temperature. The aforementioned solution A was then added, and the reaction mixture was stirred for 30 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol) to obtain the title compound (222 mg).

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.41 (1H, d, J=8.1 Hz), 4.99-4.89 (1H, m), 4.58-3.99 (7H, m), 3.69-3.42 (2H, m), 2.65-2.58 (2H, m), 2.36-2.26 (1H, m), 2.22-2.07 (3H, m), 2.05-2.00 (1H, m), 1.93-1.73 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45-1.44 (9H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=785.8/2.79 min^(B)

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 as the starting material by the same method described in Reference Example 117 to obtain each of Reference Example compounds 118 to 119 shown in Table 2-20.

TABLE 2-20 Reference Example Structural formula NMR and/or LCMS 118

LCMS: [M + H]⁺/Rt = 785.8/2.94 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.43 (1H, d, J = 8.1 Hz), 5.14- 4.94 (2H, m), 4.57-4.03 (6H, m), 3.65- 3.42 (2H, m), 2.65-2.59 (2H, m), 2.36- 2.14 (3H, m), 2.04-1.76 (4H, m), 1.61- 1.42 (27H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 119

LCMS: [M + H]⁺/Rt = 785.8/2.87 min^(B) ¹H-NMR (CDCl₃) δ: 8.65 (1H, br), 7.22 (1H, d, J = 8.1 Hz), 6.43 (1H, d, J = 8.1 Hz), 5.00-4.88 (1H, m), 4.59- 4.05 (7H, m), 3.62-3.43 (2H, m), 2.64- 2.56 (2H, m), 2.36-2.26 (1H, m). 2.19- 2.00 (4H, m), 1.92-1.77 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

Reference Example 120: Tert-butyl (2S,4S)-4-amino-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Reference Example 120-1: Tert-butyl (2S,4S)-4-azido-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Palladium on carbon (40 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (6 mL) of the compound of Reference Example 1-7 (400 mg, 0.567 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in DMF (6 mL). cis-4-azido-(tert-butoxycarbonyl)-L-proline (160 mg, 0.624 mmol), HATU (259 mg, 0.680 mmol), and triethylamine (236 μL, 1.70 mmol) were added, and the reaction mixture was stirred for 30 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (392 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.40 (1H, d, J=8.1 Hz), 5.00-4.89 (1H, m), 4.82-4.01 (7H, m), 3.86-3.76 (1H, m), 3.39-3.32 (1H, m), 2.64-2.58 (2H, m), 2.48-2.28 (2H, m), 2.22-2.14 (1H, m), 2.04-2.00 (1H, m), 1.93-1.77 (3H, m), 1.56 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=810.8/3.02 min^(B)

Reference Example 120: Tert-butyl (2S,4S)-4-amino-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Palladium on carbon (40 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (5 mL) of the compound of Reference Example 120-1 (392 mg, 0.484 mmol), and the reaction mixture was stirred for 3 hours under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methanol, and the combined filtrate was concentrated. The residue was dissolved in acetonitrile (10 mL) and further filtered through cellulose. The filtered substance was washed with acetonitrile and the combined filtrate was concentrated to obtain the title compound (355 mg) as a brown solid.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.41 (1H, d, J=8.1 Hz), 5.00-4.89 (2H, m), 4.52-4.02 (5H, m), 3.68-3.49 (2H, m), 3.33-3.29 (1H, m), 2.64-2.61 (2H, m), 2.36-2.26 (2H, m), 2.20-2.14 (1H, m), 2.04-2.01 (1H, m), 1.93-1.73 (3H, m), 1.61 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=785.0/2.28 min^(B)

Reference Example 121: Tert-butyl (2S,4S)-4-acetamido-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Triethylamine (101 μL, 0.727 mmol) and acetyl chloride (19 μL, 0.267 mmol) were added to a THF solution (2.4 mL) of the compound of Reference Example 120 (190 mg, 0.242 mmol), and the reaction mixture was stirred for 30 minutes. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (methylene chloride/methanol) to obtain the title compound (204 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 8.38-8.23 (1H, m), 7.23 (1H, d, J=8.1 Hz), 6.43 (1H, d, J=8.1 Hz), 5.12-4.93 (2H, m), 4.72-4.63 (1H, m), 4.53-4.46 (1H, m), 4.32-4.02 (4H, m), 3.61-3.45 (2H, m), 2.65-2.59 (2H, m), 2.37-2.27 (2H, m), 2.21-2.14 (1H, m), 2.04-2.00 (1H, m), 1.98-1.78 (6H, m), 1.57 (9H, s), 1.54 (9H, s), 1.46-1.43 (9H, m), 1.36 (3H, s), 1.26 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=827.0/2.86 min^(B)

Reference Example 122: Tert-butyl (2S,4R)-4-amino-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Reference Example 122-1: Tert-butyl (2S,4R)-4-azido-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

Palladium on carbon (40 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (6 mL) of the compound of Reference Example 1-7 (400 mg, 0.567 mmol), and the reaction mixture was stirred for 30 minutes under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methylene chloride, and the combined filtrate was concentrated. The resulting residue was dissolved in DMF (6 mL). (2S,4R)-4-azido-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (189 mg, 0.737 mmol), HATU (259 mg, 0.680 mmol), and triethylamine (236 μL, 1.70 mmol) were added, and the reaction mixture was stirred for 30 minutes at room temperature. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (397 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J=8.1 Hz), 6.41 (1H, d, J=8.1 Hz), 5.00-4.00 (8H, m), 3.75-3.45 (2H, m), 2.74-2.58 (2H, m), 2.36-2.12 (4H, m), 2.05-2.00 (1H, m), 1.92-1.77 (2H, m), 1.60-1.54 (18H, m), 1.46-1.44 (9H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=810.7/3.05 min^(B)

Reference Example 122: Tert-butyl (2S,4R)-4-amino-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 122-1 (397 mg, 0.490 mmol) as the starting material by the same method described in Reference Example 120 to obtain the title compound (368 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.40 (1H, d, J=8.1 Hz), 5.50-3.50 (9H, m), 3.26-3.07 (1H, m), 2.74-2.58 (2H, in), 2.36-2.28 (1H, m), 2.22-2.00 (3H, m), 1.92-1.77 (3H, m), 1.60-1.54 (18H, m), 1.45 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.17-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=784.8/2.27 min²

Reference Example 123: Tert-butyl (2S,4R)-4-acetamido-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidine-1-carbonyl}pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 122 (181 mg, 0.232 mmol) as the starting material by the same method described in Reference Example 121 to obtain the title compound (162 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.1 Hz), 6.42 (1H, d, J=8.1 Hz), 5.63-5.49 (1H, m), 5.00-3.94 (8H, m), 3.81-3.70 (1H, m), 3.48-3.32 (1H, m), 2.64-2.58 (2H, m), 2.36-2.14 (4H, m), 2.05-2.00 (1H, m), 1.98 (3H, s), 1.93-1.77 (2H, m), 1.56 (9H, s), 1.54 (9H, s), 1.47-1.43 (9H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=826.7/2.81 min

Reference Example 124: Tert-butyl (2S,4R)-4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

Reference Example 124-1: Benzyl (2S)-2-(dimethylcarbamoyl)-4-oxopyrrolidine-1-carboxylate

Triethylamine (0.48 mL, 3.44 mmol), HATU (873 mg, 2.30 mmol), and aqueous dimethylamine solution (about 9.5 mol/L, 0.24 mL, 2.3 mmol) were added to a THF solution (5.7 mL) of (2S)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylic acid (302 mg, 1.15 mmol) while cooling with ice, and the reaction mixture was stirred for 8 hours at room temperature. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (285 mg) as a colorless oily compound.

LCMS: [M+H]⁺/Rt=291.14/0.582 min^(A)

Reference Example 124-2: Benzyl (2S)-2-(dimethylcarbamoyl)-4-(2-ethoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

An n-butyl lithium/hexane solution (1.57 mol/L, 1.38 mL, 2.16 mmol) was slowly added to a THE solution (4.9 mL) of ethyl dimethylphosphonoacetate (423 mg, 2.16 mmol) at 78° C., and the reaction mixture was stirred for 30 minutes. A THE solution (4 ml) of the compound of Reference Example 124-1 (285 mg, 0.983 mmol) was added to the reaction solution at −78° C., and the reaction mixture was stirred for 5 hours at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (190 mg) as a colorless oil.

LCMS: [M+H]⁺/Rt=361.19/0.757 min^(A), 361.19/0.795 min^(A) (E/Z isomer mixture)

Reference Example 124-3: Ethyl [(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetate

A palladium on carbon-ethylenediamine complex (180 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (3.8 mL) of the compound of Reference Example 124-2 (190 mg, 0.526 mmol), and the reaction mixture was stirred for 7.5 hours under a hydrogen atmosphere. The reaction solution was filtered through celite. The filtered substance was washed with methanol, and the combined filtrate was concentrated to obtain the title compound (116.3 mg) as a colorless oil.

¹H-NMR (CDCl₃) δ: 4.05 (2H, q, J=7.1 Hz), 3.89 (1H, t, J=7.9 Hz), 3.02 (1H, dd, J=10.4, 6.7 Hz), 2.94 (3H, s), 2.91 (3H, s), 2.76 (1H, dd, J=10.4, 7.3 Hz), 2.57-2.48 (1H, m), 2.38-2.30 (3H, m), 2.23 (1H, dd, J=15.9, 7.9 Hz), 1.18 (3H, t, J=7.0 Hz).

LCMS: [M+H]⁺/Rt=229.12/0.244 min^(A)

Reference Example 124-4: Tert-butyl (2S,4R)-2-(dimethylcarbamoyl)-4-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Sodium hydrogen carbonate (128 mg, 1.53 mmol) and di-tert-butyl dicarbonate (0.237 mL, 1.02 mmol) were added to a THF-water (1:1) mixture solution (3 mL) of the compound of Reference Example 124-3 (116 mg, 0.509 mmol), and the reaction mixture was stirred for 14 hours at room temperature. The reaction solution was extracted with ethyl acetate. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (125 mg) as a colorless oil.

¹H-NMR (CDCl₃) δ: 5.25 (1H, s), 4.00-3.94 (1H, m), 3.78-3.72 (1H, m), 3.76 (3H, s), 3.17 (1H, s), 1.46 (3H, s), 1.43 (9H, s).

Reference Example 124-5: [(3R,5S)-1-(tert-butoxycarbonyl)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetic Acid

An aqueous 2 N sodium hydroxide solution (0.38 mL, 0.76 mmol) was added to a THF-water (2:1) mixture solution (1.8 mL) of the compound of Reference Example 124-4 (125 mg, 0.380 mmol) while cooling with ice, and the reaction mixture was stirred for 16 hours at room temperature. 1 N hydrochloric acid was added to the reaction solution, which was extracted with chloroform. The organic phase was washed with saturated saline, dried over sodium sulfate, filtered, and concentrated to obtain the title compound (114 mg) as a white solid.

¹H-NMR (CDCl₃) δ: 4.54 (1H, dt, J=38.8, 7.9 Hz), 3.82-3.73 (1H, m), 3.11 (1H, td, J=9.6, 4.9 Hz), 3.04-2.97 (3H, m), 2.91 (3H, s), 2.54-2.35 (3H, m), 1.60-1.50 (2H, m), 1.35 (9H, d, J=23.3 Hz).

Reference Example 124: Tert-butyl (2S,4R)-4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (145 mg, 0.253 mmol) and the compound of Reference Example 124-5 (114 mg, 0.380 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (167 mg) as a colorless amorphous compound.

LCMS: [M+H]⁺/RT=854.45/1.398 min^(C)

Reference Example 125: Tert-butyl (2R,4S)-4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

Reference Example 125-1: Tert-butyl (2R)-2-(dimethylcarbamoyl)-4-(2-ethoxy-2-oxoethylidene)pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using tert-butyl (R)-2-(dimethylcarbamoyl)-4-oxopyrrolidine-1-carboxylate (325 mg, 1.27 mmol) as the starting material by the same method described in Reference Example 124-2 to obtain the title compound (167 mg) as a colorless oil.

LCMS: [M+H]⁺/Rt=327.24/0.704 min^(A), 327.24/0.748 min^(A) (two peaks detected due to being an E/Z isomer mixture)

Reference Example 125-2: Tert-butyl (2R,4S)-2-(dimethylcarbamoyl)-4-(2-ethoxy-2-oxoethyl)pyrrolidine-1-carboxylate

A reaction and work-up were performed using the compound of Reference Example 125-1 (167 mg, 0.511 mmol) was used as the starting material by the same method described in Reference Example 124-3 to obtain the title compound (128 mg) as a colorless oil.

LCMS: [M+H]⁺/Rt=329.18/0.681 min^(A)

Reference Example 125-3: [(3S,5R)-1-(tert-butoxycarbonyl)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetic Acid

A reaction and work-up were performed using the compound of Reference Example 125-2 (128 mg, 0.388 mmol) as the starting materials by the same method described in Reference Example 124-4 to obtain the title compound (117 mg) as a white solid.

¹H-NMR (CDCl₃) δ: 4.55 (1H, dt, J=39.1, 7.9 Hz), 3.82-3.73 (1H, m), 3.10 (1H, dd, J=11.3, 7.6 Hz), 3.02 (3H, d, J=16.4 Hz), 2.91 (3H, d, J=1.2 Hz), 2.52-2.39 (3H, m), 1.60-1.50 (2H, m), 1.35 (9H, d, J=23.2 Hz).

Reference Example 125: tert-butyl (2R,4S)-4-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (149 mg, 0.260 mmol) and the compound of Reference Example 125-3 (116 mg, 0.386 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (153 mg) as a colorless amorphous compound.

LCMS: [M+H]⁺/RT=854.47/1.398 min^(C)

Reference Example 126: Tert-butyl 2-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1,1-dioxo-1λ⁶-thiomorpholine-4-carboxylate

Reference Example 126-1: [4-(tert-butoxycarbonyl)-1,1-dioxo-λ1λ⁶-thiomorpholin-2-yl]acetic Acid

An aqueous 2 N sodium hydroxide solution (1.15 mL, 2.31 mmol) was added to a methanol solution (7 mL) of tert-butyl 2-(2-ethoxy-2-oxoethyl)thiomorpholine-4-carboxylate 1,1-dioxide (247 mg, 0.769 mmol) while cooling with ice, and the reaction mixture was stirred for 4.5 hours at room temperature. An aqueous 2 N sodium hydroxide solution (1.15 mL, 2.31 mmol) was further added, and the reaction mixture was stirred for 2 hours. 1 N hydrochloric acid was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered, and concentrated to obtain the title compound (225 mg) as a light yellow oily compound.

LCMS: [M+H]⁺/RT=292.13/0.521 min^(C)

Reference Example 126: Tert-butyl 2-(2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1,1-dioxo-1λ⁶-thiomorpholine-4-carboxylate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 (0.30 g, 0.493 mmol) and the compound of Reference Example 126-1 (159 mg, 0.543 mmol) as the starting materials by the same method described in Reference Example 36-4 to obtain the title compound (225 mg) as a light yellow oil.

¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J=8.7 Hz), 6.40 (1H, d, J=8.7 Hz), 4.97-4.91 (1H, m), 4.56-4.35 (3H, m), 4.31-4.16 (5H, m), 4.09-3.98 (2H, m), 3.05-3.00 (2H, m), 2.79 (1H, d, J=16.0 Hz), 2.62 (2H, t, J=8.2 Hz), 2.35-2.28 (1H, m), 2.22-2.15 (1H, m), 2.04-2.00 (1H, m), 1.95-1.85 (2H, m), 1.81 (1H, d, J=14.6 Hz), 1.56 (9H, s), 1.54 (9H, s), 1.47 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.11 (2H, t, J=8.2 Hz), 1.03 (1H, d, J=11.0 Hz), 0.83 (3H, s).

Reference Example 127: Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 (200 mg, 0.283 mmol) as the starting material by the same method described in Reference Example 40 to obtain the title compound (119 mg).

¹H-NMR (CDCl₃) δ: 10.76 (1H, br), 7.23 (1H, d, J=8.1 Hz), 7.19 (1H, s), 7.13 (1H, s), 6.46 (1H, d, J=8.1 Hz), 5.15-4.99 (2H, m), 4.76-4.70 (1H, m), 4.60-4.54 (1H, m), 4.29-4.23 (2H, m), 2.65-2.59 (2H, m), 2.36-2.26 (1H, m), 2.23-2.14 (1H, m), 2.05-2.01 (1H, m), 1.93-1.78 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.36 (3H, s), 1.29 (3H, s), 1.15-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=666.9/2.83 min;

Reference Example 128: N²-(tert-butoxycarbonyl)-N-[(2R)-1-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide

Reference Example 128-1: Benzyl N-(tert-butoxycarbonyl)-D-seryl-D-alaninate

4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (809 mg, 2.92 mmol), triethylamine (0.355 mL, 2.56 mmol), and D-alanine benzyl p-toluenesulfonate (899 mg, 2.56 mmol) were added to a methanol (24 mL) solution of N-(tert-butoxycarbonyl)-D-serine (500 mg, 2.44 mmol), and the reaction mixture was stirred for 13 hours at room temperature. Water was added to the reaction solution, which was extracted with methylene chloride and then washed with 1 N hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution. The resultant was dried over anhydrous sodium sulfate, filtered, and concentrated to obtain the title compound (955 mg).

¹H-NMR (CDCl₃) δ: 7.42-7.31 (5H, m), 7.03-7.00 (1H, m), 5.53-5.50 (1H, m), 5.23-5.13 (2H, m), 4.70-4.55 (1H, m), 4.23-4.15 (1H, m), 4.09-3.94 (1H, m), 3.68-3.59 (1H, m), 3.11-3.03 (1H, m), 1.45-1.42 (12H, m).

LCMS: [M+H]⁺/Rt=367.2/1.77 min^(B)

Reference Example 128-2: N-(tert-butoxycarbonyl)-D-seryl-D-alanine

10% palladium on carbon (48 mg) was added to a methanol (18 mL) solution of the compound of Reference Example 128-1 (955 mg, 2.61 mmol). The reaction mixture was subjected to hydrogen substitution and was stirred for 2 hours at room temperature. After the reaction solution was filtered, the filtrate was concentrated to obtain the title compound (735 mg).

¹H-NMR (CDCl₃) δ: 7.50-7.42 (1H, m), 5.75-5.72 (1H, m), 4.62-4.51 (1H, m), 4.30 (1H, br), 4.03-3.66 (3H, m), 1.47-1.44 (12H, m).

LCMS: [M+H]⁺/Rt=277.1/1.04 min^(B)

Reference Example 128: N²-(tert-butoxycarbonyl)-N-[(2R)-1-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 (200 mg, 0.283 mmol) and the compound of Reference Example 128-2 (86.1 mg, 0.312 mmol) as the starting materials by the same method described in Reference Example 117 to obtain the title compound (203 mg).

¹H-NMR (CDCl₃) δ: 7.24 (1H, d, J=8.1 Hz), 6.92-6.82 (1H, m), 6.41 (1H, d, J=8.1 Hz), 5.46-5.37 (1H, m), 5.02-4.95 (1H, m), 4.72-4.66 (1H, m), 4.51-3.94 (7H, m), 3.65-3.32 (2H, m), 2.65-2.49 (2H, m), 2.36-2.28 (1H, m), 2.22-2.13 (1H, m), 2.05-2.00 (1H, m), 1.93-1.77 (2H, m), 1.57 (9H, s), 1.54 (9H, s), 1.45 (9H, s), 1.36-1.23 (9H, m), 1.14-1.01 (3H, m), 0.84 (3H, s).

LCMS: [M+H]⁺/Rt=830.4/2.80 min^(B)

A reaction, work-up, and purification were performed using N^(α)-(tert-butoxycarbonyl)-D-asparagine and tert-butyl N^(α)-(tert-butoxycarbonyl)-D-aspartate as the starting materials by the same method described in Reference Example 128-1 and Reference Example 128-2 to obtain each of Reference Example compounds 129 and 130 shown in Table 2-21.

TABLE 2-21 Reference Example Starting material Structural formula NMR and/or LCMS 129 N^(α)-(tert- butoxycarbonyl)- D-asparagine

LCMS: [M + H]⁺/Rt = 304.1/1.03 min^(B) ¹H-NMR (DMSO-d₆) δ: 12.6 (1H, br), 8.01 (1H, d, J = 8.1 Hz), 7.24 (1H, br), 6.91-6.88 (1H, m), 4.30-4.15 (2H, m), 3.42-3.35 (1H, m), 2.52-2.28 (2H, m), 1.37 (9H, s), 1.26 (3H, d, J = 8.1 Hz). 130 tert-Butyl N^(α)-(tert- butoxycarbonyl)- D-aspartate

LCMS: [M + H]⁺/Rt = 361.2/1.71 min^(B) ¹H-NMR (CDCl₃) δ: 7.19 (1H, d, J = 5.4 Hz), 6.75 (1H, d, J = 8.1 Hz), 4.64-4.46 (2H, m), 2.89-2.57 (2H, m), 1.47-1.45 (21H, m).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-7 and a corresponding commercially available carboxylic acid or the compound of Reference Example 129 as the starting materials by the same method described in Reference Example 42 to obtain each of Reference Example compounds 131 to 134 shown in Table 2-22.

TABLE 2-22 Ref- erence Ex- ample Structural formula NMR and/or LCMS 131

LCMS: [M + H]⁺/Rt = 814.9/2.79 min^(B) ¹H-NMR (CDCl₃) δ: 7.23 (1H, d, J = 8.1 Hz), 6.64- 6.39 (2H, m), 5.50-5.39 (1H, m), 5.01-4.91 (1H, m), 4.63- 4.00 (6H, m), 3.79-3.56 (1H, m), 3.07-2.83 (1H, m), 2.64- 2.58 (2H, m), 2.37-2.26 (1H, m), 2.23-2.13 (1H, m), 2.05- 1.77 (8H, m), 1.59-1.54 (18H, m), 1.44 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.01 (3H, m), 0.84 (3H, s). 132

LCMS: [M + H]⁺/Rt = 786.8/2.77 min^(B) ¹H-NMR (CDCl₃) δ: 7.24- 7.20 (1H, m), 7.00-6.86 (1H, m), 6.41 (1H, d, J = 8.1 Hz), 6.34-6.07 (1H, m), 5.43-5.35 (1H, m), 4.98-4.89 (1H, m), 4.63-4.31 (3H, m), 4.26-4.22 (1H, m), 4.17-4.00 (2H, m), 2.96-2.83 (1H, m), 2.64-2.58 (2H, m), 2.44-2.27 (2H, m), 2.21-2.13 (1H, m), 2.05-2.00 (1H, m, 1.93-1.76 (2H, m), 1.59-1.53 (18H, m), 1.45 (9H, s), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.00 (3H, m), 0.83 (3H, s). 133

LCMS: [M + H]⁺/Rt = 814.8/2.88 min^(B) ¹H-NMR (CDCl₃) δ: 7.24 (1H, d, J = 8.1 Hz), 6.80-6.70 (1H, m), 6.41 (1H, d, J = 8.1 Hz), 5.05-4.90 (2H, m), 4.71- 4.03 (7H, m), 2.65-2.59 (2H, m), 2.37-2.27 (1H, m), 2.22- 2.13 (1H, m), 2.05-2.00 (1H, m), 1.93-1.76 (2H, m), 1.59- 1.54 (18H, m), 1.45-1.44 (9H, m), 1.36-1.26 (12H, m), 1.14-1.01 (3H, m), 0.84 (3H, s). 134

LCMS: [M + H]⁺/Rt = 857.8/2.71 min^(B) ¹H-NMR (CDCl₃) δ: 7.40- 7.31 (1H, m), 7.23 (1H, d, J = 8.1 Hz), 6.41 (1H, d, J = 8.1 Hz), 6.09-5.95 (1H, m), 5.90-5.79 (1H, m), 5.51-5.41 (1H, m), 5.01-4.92 (1H, m), 4.70-4.00 (7H, m), 2.97-2.88 (1H, m), 2.64-2.48 (3H, m), 2.37-2.27 (1H, m), 2.22-2.13 (1H, m), 2.05-2.00 (1H, m), 1.93-1.77 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.46-1.45 (9H, m), 1.36 (3H, s), 1.32- 1.23 (6H, m), 1.14-1.01 (3H, m), 0.84 (3H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 and a corresponding commercially available carboxylic acid or the compound of Reference Example 130 as the starting materials by the same method described in Reference Example 3 to obtain each of Reference Example compounds 135 to 137 shown in Table 2-23.

TABLE 2-23 Refer- ence Exam- ple Structural formula NMR and/or LCMS 135

LCMS: [M + H]⁺/Rt = 800.7/2.83 min^(B) ¹H-NMR (CDCl₃) δ: 7.26-7.21 (1H, m), 6.77-6.68 (1H, m), 6.41 (1H, d, J = 8.1 Hz), 5.10-4.92 (2H, m), 4.72-4.03 (6H, m), 3.85-3.76 (2H, m), 2.65-2.59 (2H, m), 2.36-2.28 (1H, m), 2.22-2.12 (1H, m), 2.04- 2.00 (1H, m), 1.93-1.76 (2H, m), 1.56-1.54 (18H, m), 1.46 (9H, s), 1.36-1.28 (9H, m), 1.14-1.01 (3H, m), 0.84 (3H, s). 136

LCMS: [M + H]⁺/Rt = 914.7/3.07 min^(B) ¹H-NMR (CDCl₃) δ: 7.24-7.03 (1H, m), 6.42-6.38 (1H, m), 5.66-5.53 (1H, m), 4.99-4.91 (1H, m), 4.69- 4.04 (8H, m), 2.94-2.82 (1H, m), 2.64-2.55 (3H, m), 2.36-2.27 (1H, m), 2.20-2.12 (1H, m), 2.05-2.00 (1H, m), 1.93-1.77 (2H, m), 1.59- 1.53 (18H, m), 1.46-1.43 (18H, m), 1.36 (3H, s), 1.32-1.23 (6H, m), 1.14-1.01 (3H, m), 0.84 (3H, s). 137

LCMS: [M + H]⁺/Rt = 843.6/3.14 min^(B) ¹H-NMR (CDCl₃) δ: 7.22 (1H, d, J = 8.1 Hz), 6.40 (1H, d, J = 8.1 Hz), 5.75-5.67 (1H, m), 4.94-4.89 (1H, m), 4.48-4.32 (3H, m), 4.26-4.22 (1H, m), 4.19-4.11 (1H, m), 4.07- 4.02 (1H, m), 2.86-2.71 (1H, m), 2.64-2.48 (3H, m), 2.37-2.26 (1H, m), 2.23-2.13 (1H, m), 2.05-2.00 (1H, m), 1.92-1.77 (2H, m), 1.56 (9H, s), 1.53 (9H, s), 1.46-1.43 (18H, m), 1.36 (3H, s), 1.28 (3H, s), 1.14-1.00 (3H, m), 0.83 (3H, s).

Reference Example 138: Tert-butyl 4-[2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-1-(methylamino)-2-oxoethyl]-1H-imidazole-1-carboxylate

Reference Example 138-1: {[(benzyloxy)carbonyl]amino}(1H-imidazol-4-yl)acetic Acid

Sodium hydrogen carbonate (5.78 g, 68.8 mmol) and benzyl chloroformate (5.87 g, 34.4 mmol) were added to an ethanol/water (1:1) mixture solution (57 mL) of the compound of Reference Example 36-2 (3.68 g, 17.2 mmol) while cooling with ice. After stirring for 15 minutes, the reaction solution was warmed up to room temperature, and stirred for another 12 hours. Saturated ammonium chloride water was added to the reaction solution, which was extracted with ethanol (40 mL) and dichloromethane (40 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by chromatography (dichloromethane/methanol=10/1) to obtain the title compound (1.7 g).

¹H-NMR (500 MHz, CDCl₃) δ: 8.86-8.82 (1H, m), 7.51-7.47 (1H, m), 7.37-7.24 (5H, m), 5.57 (1H, s), 5.10 (2H, s).

Reference Example 138-2: Tert-butyl 6-({1-[{[(benzyloxy)carbonyl]amino}(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Triethylamine (5 mL, 18 mmol), ethyldicarbodiimide (1.16 g, 6 mmol), and 1-hydroxybenzotriazole (1.64 g, 12 mmol) were added to a DMF (24 mL) solution of the compound of Reference Example 138-1 (1.7 g, 6.1 mmol) and the compound of Reference Example 1-8 (1.7 g, 3.0 mmol), and the reaction mixture was stirred for 12 hours at room temperature. A saturated aqueous sodium hydrogen carbonate solution (30 mL) was added to the reaction solution, which was extracted with ethyl acetate (30 mL). The organic phase was washed with saturated saline (30 mL), then dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by column chromatography (dichloromethane/methanol=50/1) to obtain the title compound (956 mg).

¹H-NMR (500 MHz, CDCl₃) δ: 9.30 (1H, brs), 7.59 (1H, s), 7.40-7.22 (5H, m), 7.21-7.05 (2H, m), 6.03 (1H, brs), 5.48-5.32 (2H, m), 5.15-5.08 (4H, m), 4.43-4.06 (2H, m), 3.79-3.67 (3H, m), 2.63-1.79 (3H, m), 1.54 (9H, s), 1.53 (9H, s),

1.36-1.16 (6H, m), 1.13-1.01 (2H, m), 0.89-0.80 (4H, m).

Reference Example 138-3: Tert-butyl 4-(1-{[(benzyloxy)carbonyl]amino}-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1H-imidazole-1-carboxylate

Triethylamine (0.641 mL, 4.6 mmol) and di-tert-butyl dicarbonate (503 mg, 2.3 mmol) were added to a dichloromethane (5.75 mL) solution of the compound of Reference Example 138-2 (956 mg, 1.15 mmol), and the reaction mixture was stirred overnight at room temperature. A saturated aqueous ammonium chloride solution (10 mL) was added to the reaction solution, which was extracted with dichloromethane (10 mL). The organic phase was dried over sodium sulfate, then filtered and concentrated. The resulting residue was purified by column chromatography (dichloromethane/methanol=50/1) to obtain the title compound (228 mg).

¹H-NMR (500 MHz, CDCl₃) δ: 8.02-7.98 (1H, m), 7.38-7.12 (7H, m), 6.39-6.07 (1H, m), 5.32-4.05 (5H, m), 3.50-3.49 (1H, m), 2.63-1.78 (7H, m), 1.62 (9H, s), 1.56 (9H, s), 1.52 (9H, s), 1.38-1.23 (8H, m), 1.15-1.08 (2H, m), 1.05-0.83 (5H, m).

Reference Example 138-4: Tert-butyl 4-(1-amino-2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-2-oxoethyl)-1H-imidazole-1-carboxylate

Palladium hydroxide (22 mg) was added to a methanol solution (4 mL) of the compound of Reference Example 138-3 (228 mg, 0.245 mmol), and the reaction mixture was stirred under a hydrogen atmosphere at room temperature. After 12 hours, the reaction solution was filtered through celite, and the filtrate was concentrated. The resulting residue was purified by column chromatography (dichloromethane/methanol=50/1) to obtain the title compound (123 mg).

¹H-NMR (500 MHz, CDCl₃) δ: 8.02-8.00 (1H, m), 7.35-7.20 (2H, m), 6.40-6.37 (1H, m), 4.96-4.90 (1H, brs), 4.45-4.39 (m, 1H), 4.25-4.20 (1H, m), 4.13-4.11 (1H, m), 2.63-2.60 (2H, m), 2.35-2.28 (1H, m), 2.17-2.14 (1H. m), 2.03-2.01 (1H, m), 1.61 (9H, s), 1.56 (9H, s), 1.52 (9H, s), 1.28-1.26 (6H, m), 1.13-1.10 (1H, m), 0.83 (6H, s).

Reference Example 138: Tert-butyl 4-[2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-1-(methylamino)-2-oxoethyl]-1H-imidazole-1-carboxylate

A formalin solution (30% methanol solution, 2.32 μL, 0.231 mmol) was added to a diethyl ether solution (3 mL) of the compound of Reference Example 138-4 (123 mg, 0.154 mmol), and the reaction mixture was stirred for 1.5 hours at room temperature. Dichloromethane (10 mL) was added to the reaction solution. The organic layer was washed three times with water (10 mL), dried over sodium sulfate, then filtered and concentrated. Sodium triacetoxyborohydride (65 mg, 0.308 mmol) was added to a dichloromethane/acetic acid (1:1) mixture solution (3 mL) of the resulting residue, and the reaction mixture was stirred for 1.5 hours at room temperature. The reaction solution was added to a saturated aqueous sodium hydrogen carbonate solution (10 mL) and extracted with dichloromethane (10 mL). The retrieved organic layer was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by preparative thin-layer chromatography (dichloromethane/methanol=10/1) to obtain the compound of Reference Example 138 (26 mg) and the compound of Reference Example 139 (42 mg).

¹H-NMR (500 MHz, CDCl₃) δ: 8.00 (1H, d, J=6.3 Hz), 7.35 (1H, d, J=8.6 Hz), 7.24-7.15 (1H, m), 6.38 (1H, dd, J=8.6, 8.3 Hz), 4.95-4.72 (1H, m), 4.66-4.05 (4H, m), 2.63-2.58 (2H, m), 2.41 (3H, s), 2.35-1.78 (5H, m), 1.47 (9H, s), 1.52 (9H, s), 1.52 (9H, s), 1.35 (3H, s), 1.28 (3H, s), 1.28-1.23 (2H, m), 1.24-1.08 (2H, m), 1.04-1.02 (1H, m), 0.83 (3H, s).

Reference Example 139: Tert-butyl 4-[2-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-1-(dimethylamino)-2-oxoethyl]-1H-imidazole-1-carboxylate

¹H-NMR (500 MHz, CDCl₃) δ: 8.04-8.03 (1H, m), 7.52-7.49 (1H, m), 7.21-7.19 (1H, m), 6.39-6.37 (1H, m), 4.91-3.98 (6H, m), 2.63-2.58 (2H, m), 2.35-1.78 (11H, m), 1.56 (9H, s), 1.53 (9H, s), 1.52 (9H, s), 1.35-1.23 (5H, m), 1.14-1.03 (3H, m), 0.83 (4H, s).

A reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 3 to obtain each of Reference Example compounds 140 to 147 shown in Tables 2-24 and 2-25. Further, a reaction, work-up, and purification were performed using the compound of Reference Example 1-8 as the starting material by the same method described in Reference Example 36-4 to obtain Reference Example compounds 148 and 149 shown in Table 2-26.

TABLE 2-24 Reference Example Structural formula NMR and/or LCMS 140

LCMS: [M + H]⁺/Rt = 773.00/1.394 min^(A1) H-NMR (CD₃OD) δ: 7.39-7.26 (6H, m), 6.67 (1H, d, J = 8.5 Hz), 5.12-5.05 (3H, m), 4.39-4.33 (1H, m), 4.29 (2H, d, J = 8.5 Hz), 4.00-3.94 (1H, m), 3.74-3.67 (2H, m), 3.34 (2H, s), 2.58 (2H, t, J = 7.9 Hz), 2.39-2.32 (1H, m), 2.21-2.16 (1H, m), 1.99 (1H, t, J = 5.5 Hz), 1.89-1.87 (1H, m), 1.79 (1H, d, J = 15.3 Hz), 1.55 (9H, d, J = 7.9 Hz), 1.52 (9H, s), 1.35 (3H, s), 1.29 (3H, s), 1.08 (2H, t, J = 8.2 Hz), 0.99 (1H, d, J = 10.4 Hz), 0.86 (3H, s). 141

LCMS: [M + H]⁺/Rt = 773/2.275 min^(H)

TABLE 2-25 142

LCMS: [M + H]⁺/Rt = 905/2.433 min^(H) 143

LCMS: [M + H]⁺/Rt = 812/2.217 min^(H) 144

LCMS: [M + H]⁺/Rt = 877/2.150 min^(H) 145

LCMS: [M + H]⁺/Rt = 892/1.411 min^(E) 146

LCMS: [M + H]⁺/Rt = 857.7/3.17 min^(B) 147

LCMS: [M + H]⁺/Rt = 800.7/2.81 min^(B)

TABLE 2-26 148

LCMS: [M + H]⁺/Rt = 773.54/3.960 min^(I) 149

LCMS: [M + H]⁺/Rt = 773.54/3.940 min^(I)

Reference Example 150: (4S)-4-[(tert-butoxycarbonyl)amino]-6-{3-[2-(tert-butoxycarbonyl)-3-[(tert-butoxycarbonyl)oxy]-4-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}phenoxy]azetidin-1-yl}-6-oxohexanoic Acid

10% palladium on carbon (113 mg) was added to a methanol (7 mL) solution of the compound of Reference Example 142 (334 mg, 0.369 mmol). The reaction mixture was subjected to hydrogen substitution and was stirred for 2 hours at room temperature. After filtering the reaction solution, the filtrate was concentrated to obtain the title compound (329 mg).

LCMS: [M+H]⁺/Rt=815.5/2.211 min^(H)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 144 and 145 as the starting materials by the same method described in Reference Example 151 to obtain Reference Example compounds 151 and 152 shown in Table 2-27, respectively.

TABLE 2-27 Reference Starting Example material Structural formula NMR and/or LCMS 151 Reference Example 144

LCMS: [M + H]⁺/Rt = 787/2.247 min^(H) 152 Reference Example 145

LCMS: [M + H]⁺/Rt = 801/2.231 min^(H)

Reference Example 153: Tert-butyl 6-[(1-{(3S)-6-amino-3-[(tert-butoxycarbonyl)amino]-6-oxohexanoyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

N,N-diisopropylethylamine (0.131 mL, 0.750 mmol) and HATU (107 mg, 0.281 mmol) were added to a DMF (1 mL) solution of the compound of Reference Example 150 (153 mg, 0.188 mmol), and the reaction mixture was stirred for 30 minutes at room temperature. Ammonium chloride (16.1 mg, 0,300 mmol) was added, and the reaction mixture was stirred for 2 hours at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, which was extracted with ethyl acetate. The organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and then saturated saline, dried over sodium sulfate and filtered, and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain the title compound (45.7 mg).

LCMS: [M+H]⁺/Rt=814.5/2.204 min^(H)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 151 and 152 as the starting materials by the same method described in Reference Example 153 to obtain Reference Example compounds 154 and 155 shown in Table 2-28, respectively.

TABLE 2-28 Reference Starting Example material Structural formula NMR and/or LCMS 154 Reference Example 151

LCMS: [M + H]⁺/Rt = 786.5/2.150 min^(H) 155 Reference Example 152

LCMS: [M + H]⁺/Rt = 800.55/2.210 min^(H)

Example 1: 7-[(1-acetylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid

The compound of Reference Example 1 (105 mg) and phenylboronic acid (19 mg) were added to CPME (0.9 mL). 3 mol/L hydrochloric acid (1.14 mL) was added thereto, and the reaction mixture was stirred overnight at room temperature. The aqueous layer was concentrated and purified by reversed phase column chromatography (eluent: acetonitrile/water=1/99 to 95/5) to obtain the title compound (9.2 mg).

¹H-NMR (CD₃OD) δ: 7.16-7.08 (1H, m), 6.35-6.25 (1H, m), 5.06-4.97 (1H, m), 4.58-4.52 (1H, m), 4.37-4.30 (1H, m), 4.22-4.17 (1H, m), 3.96-3.89 (1H, m), 2.70-2.62 (2H, m), 1.86 (3H, s), 1.05-1.01 (2H, m).

Example 2: 2-hydroxy-7-({1-[(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride

Triethylsilane (0.2 mL) and, additionally, TFA (0.9 mL) was added to the compound of Reference Example 3 (96 mg) and phenylboronic acid (14 mg), and the reaction mixture was stirred for 3 hours at room temperature. After concentrating the reaction mixture, the residue was washed with a mixture solvent of diethyl ether/hexane (1:1). The resulting solid was dissolved in methanol and purified by reversed phase chromatography and concentrated. After adding 0.2 mL of aqueous 1 N hydrochloric acid solution to the residue, the mixture was concentrated to obtain the compound of interest (21.6 mg).

LCMS: [M+H]⁺/Rt=372/0.44 min^(C)

Example 3: 2-hydroxy-7-{[1-(methanesulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic

Triethylsilane (0.2 mL) and, additionally, TFA (0.9 mL) was added to the compound of Reference Example 2 (96 mg) and phenylboronic acid (14 mg), and the reaction mixture was stirred for 3 hours at room temperature. After concentrating the reaction mixture, the residue was washed with a mixture solvent of diethyl ether/hexane (1:1). The resulting solid was dissolved in methanol and purified by reversed phase chromatography and concentrated to obtain the compound of interest (28 mg).

¹H-NMR (CD₃OD) δ: 7.16-7.00 (1H, m), 6.37-6.20 (1H, m), 5.06-4.97 (1H, m), 4.31-4.25 (2H, m), 3.98-3.94 (2H, m), 2.96 (3H, s), 2.68-2.65 (2H, m), 1.05-1.01 (2H, m)

Example 4: 8-({1-[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic Acid Disodium Salt

The compound of Reference Example 17 (119 mg), phenylboronic acid (16.2 mg), acetonitrile (2.0 mL), hexane (2.0 mL), and 4 N hydrochloric acid/dioxane solution (1.0 mL) were added, and the reaction mixture was stirred for 19 hours at room temperature. After allowing it to stand, the supernatant (top layer) of the reaction solution separated into two layers was removed, and the remaining bottom layer was washed 5 times with hexane and twice with diethyl ether (the washing process removes the supernatant after standing). The solid produced in the solution at the bottom layer was washed with acetonitrile (5.0 mL). The residue of the solid obtained by removing the solvent was dried under reduced pressure. The resulting dried residue was dissolved in water. An aqueous 2 N sodium hydroxide solution (0.5 mL) was added. The mixture was purified by reversed phase column chromatography to obtain the title compound (41.7 mg) as a colorless solid.

¹H-NMR (D₂O) δ: 7.20-7.13 (2H, m), 6.83-6.75 (3H, m), 5.98-5.90 (1H, m), 5.00-4.91 (1H, m), 4.63-3.90 (5H, m), 2.59-2.50 (2H, m), 0.39-0.29 (2H, m).

A reaction, work-up, and purification were performed using Reference Example compounds 4 to 16 and 18 to 33 shown in Table 2 as the starting materials by the same method described in Example 4 to obtain each of Example compounds 5 to 33. However, if a free form is the final product (Examples 5 and 34), the free form was obtained without sodium hydroxide treatment. If a hydrochloride (hydrochloride salt) is the final product (Example 6), the hydrochloride was obtained by purifying the compound by using reversed phase chromatography and then adding hydrochloric acid and concentrating. A reaction, work-up, and purification were performed using Reference Example compound 34 as the starting material by the same method described in Example 3 to obtain Example compound 34.

TABLE 3-1 Starting Example material Structural formula NMR and/or LCMS 5 Reference Example 4

LCMS: [M + H]⁺/Rt = 447/ 0.626 min^(C) 6 Reference Example 5

¹H-NMR (CD₃OD) δ: 8.67-8.64 (1H, m), 8.06-8.01 (2H, m), 7.59-7.56 (1H, m), 7.18-7.15 (1H, m), 6.38-6.35 (1H, m), 5.13-5.10 (2H, m), 4.72-4.69 (1H, m), 4.63-4.60 (1H, m), 4.22-4.19 (1H, m), 2.70 (2H, t, J = 7.3 Hz), 1.05 (2H, t, J = 7.3 Hz). 7 Reference Example 6

¹H-NMR (D₂O) as a mixture of keto and enol forms δ: 6.87-6.82 (1H, m), 6.04- 6.02 (1H, m), 5.02-4.97 (1H, m), 4.65- 3.64 (4H, m), 3.20-3.13 (2H, m), 2.57- 2.54 (2H, m), 2.11 and 2.07 (3H, s) and 0.36-0.33 (2H, m). 8 Reference Example 7

¹H-NMR (D₂O) δ: 8.32-8.31 (1H, m), 6.94-6.92 (1H, m), 6.94-6.92 (1H, m), 5.13-5.11 (1H, m), 4.99-4.94 (1H, m), 4.65-4.59 (2H, m), 4.28-4.25 (1H, m), 2.63-2.60 (2H, m), and 0.45- 0.42 (2H, m). 9 Reference Example 8

¹H-NMR (D₂O) δ: 8.41 (1H, d, J = 6.4 Hz), 7.83 (1H, t, J = 7.8 Hz), 7.76 (1H, dd, J = 7.8, 1.8 Hz), 7.73-7.69 (1H, m), 6.91 (1H, d, J = 7.8 Hz), 6.07 (1H, d, J = 7.8 Hz), 5.15-5.10 (1H, m), 4.69-4.63 (1H, m), 4.47 (1H, dd, J = 9.6, 7.3 Hz), 4.32 (1H, dd, J = 13.3, 4.1 Hz), 4.20 (1H, dd, J = 9.6, 3.2 Hz), 2.61 (2H, t, J = 7.1 Hz), 0.44 (2H, s). 10 Reference Example 9

¹H-NMR (D₂O) as a mixture of isomers δ: 7.46-7.38 (5H, m), 6.89-6.80 (1H, m), 6.01-5.91 (1H, m), 5.04-4.93 (0.5H, m), 4.71-4.59 (1.5H, m), 4.49-4.38 (0.5H, m), 4.22-4.07 (1H, m), 4.01-3.91 (1H, m), 2.63-2.50 (2H, m), 0.45-0.30 (2H, m).

TABLE 3-2 11 Reference Example 10

¹H-NMR (D₂O) δ: 7.65-7.49 (5H, m), 6.88 (1H, d, J = 8.2 Hz), 6.04 (1H, d, J = 8.2 Hz), 5.04 (1H, td, J = 7.0, 3.7 Hz), 4.65 (1H, dd, J = 10.1, 6.4 Hz), 4.57 (1H, dd, J = 11.4, 6.9 Hz), 4.45 (1H, dd, J = 10.5, 2.7 Hz), 4.23 (1H, dd, J = 10.8, 3.4 Hz), 2.58 (2H, t, J = 6.9 Hz), 0.38 (2H, t, J = 7.1 Hz). 12 Reference Example 11

¹H-NMR (D₂O) δ: 8.72 (1H, d, J = 1.4 Hz), 8.63 (1H, dd, J = 5.0, 1.4 Hz), 8.05 (1H, dt, J = 7.8, 1.8 Hz), 7.53 (1H, dd, J = 7.8, 5.0 Hz), 6.85 (1H, d, J = 8.2 Hz), 6.01 (1H, d, J = 8.2 Hz), 5.04 (1H, td, J = 7.9, 4.7 Hz), 4.66 (1H, t, J = 8.5 Hz), 4.56 (1H, dd, J = 11.2, 6.6 Hz), 4.44 (1H, dd, J = 10.1, 3.7 Hz), 4.23 (1H, dd, J = 11.2, 3.9 Hz), 2.55 (2H, t, J = 7.1 Hz), 0.34 (2H, t, J = 6.9 Hz). 13 Reference Example 12

¹H-NMR (CD₃OD) δ: 8.85-8.78 (1H, m), 8.62-8.52 (1H, m), 8.06-7.95 (2H, m), 7.18 (1H, d, J = 8.2 Hz), 6.36 (1H, d, J = 7.9 Hz), 5.19-5.06 (1H, m), 4.83-4.70 (2H, m), 4.49- 4.38 (2H, m), 4.14-4.02 (2H, m), 2.71 (2H, t, J = 7.7 Hz), 1.07 (2H, t, J = 7.7 Hz). 14 Reference Example 13

¹H-NMR (CD₃OD)) δ: 8.87-8.74 (2H, m), 8.62-8.53 (1H, m), 8.12-8.03 (1H, m), 7.18 (1H, d, J = 8.2 Hz), 6.36 (1H, d, J = 8.2 Hz), 5.18-5.09 (1H, m), 4.82-4.70 (2H, m), 4.49- 4.36 (2H, m), 4.07-3.99 (2H, m), 2.71 (2H, t, J = 7.7 Hz), 1.07 (2H, t, J = 7.7 Hz). 15 Reference Example 14

¹H-NMR (D₂O) as a mixture of isomers δ: 7.43-7.29 (5H, m), 6.84-6.76 (1H, m), 6.01- 5.89 (1H, m), 4.95-4.83 (1H, m), 4.65-4.53 (1H, m), 4.41-3.50 (4H, m), 2.52 (2H, t, J = 6.6 Hz), 0.31 (2H, q, J = 6.4 Hz). 16 Reference Example 15

¹H-NMR (D₂O) δ: 8.32 (2H, d, J = 6.0 Hz), 7.19 (2H, d, J = 6.0 Hz), 6.74 (1H, d, J = 8.2 Hz), 5.91 (1H, d, J = 8.2 Hz), 4.91-4.80 (1H, m), 4.52-4.49 (1H, m), 4.29-4.20 (2H, m), 3.96-3.91 (1H, m), 3.52 (2H, s), 2.44 (2H, t, J = 7.1 Hz), 0.23 (2H, t, J = 7.1 Hz). 17 Reference Example 16

¹H-NMR (D₂O) δ: 7.03 (2H, d, J = 8.2 Hz), 6.86 (1H, d, J = 8.2 Hz), 6.67 (2H, d, J = 8.2 Hz), 6.01 (1H, d, J = 8.2 Hz), 4.99-4.38 (2H, m), m), 4.62-4.55 (1H, m), 4.29-4.38 (2H, m), 4.05-3.99 (1H, m), 3.46-3.36 (2H, m), 2.56 (2H, t, J = 7.1 Hz), 0.35 (2H, t, J = 7.1 Hz). 18 Reference Example 18

¹H-NMR (D₂O) δ: 8.51 (1H, s), 8.12 (1H, s), 6.94 (1H, d, J = 8.2 Hz), 6.11 (1H, d, J = 8.2 Hz), 5.20-5.05 (3H, m), 4.72-4.64 (1H, m), 4.52-4.45 (1H, m), 4.42-4.37 (1H, m), 4.20- 4.13 (1H, m), 2.62 (2H, t, J = 6.9 Hz), 0.46 (2H, t, J = 6.9 Hz).

TABLE 3-3 19 Reference Example 19

¹H-NMR (D₂O)) δ: 7.75-7.65 (1H, m), 7.42-7.35 and 7.70-7.09 (1H, m), 6.90- 6.82 (1H, m), 6.02-5.96 (1H, m), 5.05- 4.85 and 4.70-3.91 (6H, m), 2.62-2.50 (2H, m), 0.43-0.31 (2H, m). 20 Reference Example 20

¹H-NMR (D₂O) δ: 7.41-7.24 (5H, m), 6.86 (1H, d, J = 8.2 Hz), 6.02 (1H, d, J = 8.2 Hz), 5.01-4.96 (1H, m), 4.63-4.58 (1H, m), 4.40-4.32 (2H, m), 4.08-4.01 (1H, m), 3.58 (2H, s), 2.56 (2H, t, J = 7.1 Hz), 0.35 (2H, t, J = 6.9 Hz). 21 Reference Example 21

¹H-NMR (D₂O) δ: 7.39-7.28 (2H, m), 7.30-7.22 (3H, m), 6.84 (1H, d, J = 7.8 Hz), 5.92 (1H, d, J = 7.8 Hz), 4.28-4.20 (1H, m), 4.17-4.09 (1H, m), 3.98-3.88 (2H, m), 2.94-2.80 (2H, m), 2.60-2.50 (2H, m), 2.50-2.43 (2H, m), 0.40-0.31 (2H, m). 22 Reference Example 22

¹H-NMR (D₂O) δ: 7.80-7.62 (1H, m), 7.22-7.0 (2H, m), 6.96-6.85 (1H, m), 6.13-5.99 (1H, m), 5.10-5.05 (1H, m), 4.64-4.53 (1H, m), 4.47-4.38 (1H, m), 4.36-4.27 (1H, m), 4.20-4.05 (1H, m), 2.67 (2H, m), 0.50-0.38 (2H, m). 23 Reference Example 23

¹H-NMR (CD₃OD) δ: 9.18 (1H, s), 7.21- 7.14 (1H, m), 6.44-6.12 (1H, m), 5.38 (2H, s), 5.22-5.08 (1H, m), 4.80-4.69 (1H, m), 4.51-4.38 (2H, m), 4.15-4.03 (1H, m), 2.78-2.65 (2H, m), 1.14-0.98 (2H, m). 24 Reference Example 24

¹H-NMR (D₂O) δ: 6.89 (1H, d, J = 8.2 Hz), 6.05 (1H, d, J = 8.2 Hz), 5.03-4.97 (1H, m), 4.54 (1H, dd, J = 9.6, 6.9 Hz), 4.40 (1H, dd, J = 11.0, 6.9 Hz), 4.29 (1H, dd, J = 9.6, 3.7 Hz), 4.08 (1H, dd, J = 11.0, 3.7 Hz), 3.85 (1H, d, J = 16.3 Hz), 3.75 (1H, d, J = 16.3 Hz), 2.58 (2H, t, J = 6.9 Hz), 0.41 (2H, t, J = 7.1 Hz). 25 Reference Example 25

¹H-NMR (D₂O) δ: 7.41-7.21 (5H, m), 6.97-6.78 (1H, m), 5.93-5.80 (1H, m), 4.59-4.52, 4.33-4.25, 4.33-4.25, 4.18- 4.10, 4.05-3.99, 3.91-3.82, 3.74-3.65, 3.53-3.48, 3.38-3.30 (6H, m), 2.99-2.90 (1H, m), 2.88-2.72 (1H, m), 2.60-2.50 (2H, m), 0.43-0.27 (2H, m). 26 Reference Example 26

¹H-NMR (D₂O) δ: 7.14-7.01 (2H, m), 6.88-6.76 (3H, m), 5.86-5.70 (1H, m), 4.61-4.56, 4.30-4.12, 4.00-3.82, 3.63- 3.44, 2.95-2.80, 2.72-2.48 (10H, m), 0.44-0.26 (2H, m). 27 Reference Example 27

¹H-NMR (D₂O) δ: 7.69, 7.52 (1H, s), 6.93- 6.83 (2H, m), 5.99-5.78 (1H, m), 4.42- 4.07, 4.01-3.79, 3.70-3.50, 3.05-2.91 (5H, m), 2.91-2.66 (1H, m), 2.61-2.48 (2H, m), 0.42-0.28 (2H, m).

TABLE 3-4 28 Reference Example 28

¹H-NMR (D₂O) δ: 6.87 (1H, d, J = 8.2 Hz), 6.03 (1H, d, J = 8.2 Hz), 5.04-4.96 (1H, m), 4.68-4.58 (1H, m), 4.43-4.28 (2H, m), 4.08-4.00 (1H, m), 3.19-3.13 (1H, m), 2.56 (2H, t, J = 6.9 Hz), 1.81- 1.73 (1H, m), 1.00-0.81 (6H, m), 0.35 (2H, t, J = 7.1 Hz). 29 Reference Example 29

¹H-NMR (D₂O) δ: 7.73, 7.54 (1H, s), 6.98-6.80 (2H, m), 5.96-5.80 (1H, m), 4.42-4.11, 4.04-3.83, 3.74-3.66, 3.65- 3.57, 3.08-2.96 (5H, m), 2.90-2.74 (2H, m), 2.64-2.50 (2H, m), 0.84-0.31 (2H, m). 30 Reference Example 30

¹H-NMR (D₂O) δ: 7.50-7.31 (5H, m), 6.89-6.84 (1H, m), 6.03-5.95 (1H, m), 5.33-5.27 (1H, m), 5.15-4.97 (1H, m), 4.50-4.28 (2H, m), 4.20-3.95 (2H, m), 3.33 (6H, dt, J = 28.1, 9.6 Hz), 2.63- 2.48 (2H, m), 1.16-1.02 (3H, m), 0.50- 0.30 (2H, m). 31 Reference Example 31

¹H-NMR (D₂O) δ: 6.87 (1H, d, J = 7.9 Hz), 6.04 (1H, d, J = 7.9 Hz), 5.09-4.96 (1H, m), 4.90-4.84 (1H, m), 4.66-4.52 (1H, m), 4.43-4.30 (2H, m), 4.10-4.00 (1H, m), 3.93-3.80 (1H, m), 3.08-2.90 (2H, m), 2.57 (2H, t, J = 6.9 Hz), 2.28- 2.02 (1H, m), 1.93-1.68 (3H, m), 0.36 (2H, t, J = 6.9 Hz). 32 Reference Example 32

LCMS: [M + H]⁺/Rt = 361/ 0.87 min^(B) 33 Reference Example 33

¹H-NMR (D₂O) δ: 7.56 (1H, s), 6.93 (1H, s), 6.83 (1H, d, J = 8.2 Hz), 5.99 (1H, d, J = 8.2 Hz), 5.04-4.93 (1H, m), 4.57-4.48 (1H, m), 4.42-4.33 (1H, m), 4.23-4.17 (1H, m), 4.09-3.98 (1H, m), 3.14 (2H, t, J = 6.6 Hz), 2.82 (2H, t, J = 6.6 Hz), 2.52 (2H, t, J = 6.9 Hz), 0.31 (2H, t, J = 6.9 Hz). 34 Reference Example 34 +get,1360 ¹H-NMR (CD₃OD) δ: 6.96 (1H, d, J = 7.9 Hz), 6.90-6.87 (1H, m), 6.80-6.78 (2H, m), 6.58 (1H, d, J = 7.9 Hz), 4.99-4.97 (2H, m), 4.68-4.65 (1H, m), 4.48-4.45 (1H, m), 4.18-4.16 (1H, m), 2.57 (2H, t, J = 7.3 Hz), 0.51 (2H, t, J = 7.3 Hz).

The names of the compounds of Examples 5 to 34 are described below.

-   7-({1-[(2-amino-1,3-thiazol-4-yl)(methoxyimino)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 5) -   2-hydroxy-7-{[1-(pyridine-2-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 6) -   4,4-dihydroxy-8-({1-[(methylsulfanyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 7) -   4,4-dihydroxy-8-{[1-(1H-1,2,4-triazole-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 8) -   4,4-dihydroxy-8-{[1-(1-oxido-2-pyridinylcarbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 9) -   8-({1-[(2R)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 10) -   8-[(1-benzoylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 11) -   4,4-dihydroxy-8-{[1-(pyridine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 12) -   4,4-dihydroxy-8-({1-[(pyridin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 13) -   4,4-dihydroxy-8-({1-[(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 14) -   8-({1-[(2S)-2-amino-2-phenylacetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 15) -   4,4-dihydroxy-8-({1-[(pyridin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 16) -   4,4-dihydroxy-8-({1-[(4-hydroxyphenyl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 17) -   4,4-dihydroxy-8-({1-[(1H-1,2,4-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 18) -   8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 19) -   4,4-dihydroxy-8-{[1-(phenylacetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 20) -   4,4-dihydroxy-8-{[1-(3-phenylpropanoyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 21) -   4,4-dihydroxy-8-({1-[(1H-imidazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 22) -   4,4-dihydroxy-8-({1-[(1H-tetrazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 23) -   4,4-dihydroxy-8-({1-[(2H-tetrazol-5-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 24) -   4,4-dihydroxy-8-[(1-D-phenylalanylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 25) -   4,4-dihydroxy-8-[(1-D-tyrosylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 26) -   8-[(1-D-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 27) -   4,4-dihydroxy-8-[(1-D-valylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 28) -   8-[(1-L-histidylazetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 29) -   8-[(1-{(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-phenylacetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 30) -   4,4-dihydroxy-8-[(1-D-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 31) -   4,4-dihydroxy-8-[(1-L-prolylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 32) -   8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 33) -   7-{[1-(3,4-dihydroxybenzoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 34)

Example 35: 2-hydroxy-7-{[1-(hydroxycarbamoyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid

Phenylboronic acid (10.3 mg), 4 N hydrocholic acid/ethyl acetate solution, and hexane (3.6 mL) were added to an acetonitrile (0.73 mL) solution of the compound of Reference Example 35. The reaction mixture was stirred for 7 hours at room temperature and allowed to stand overnight. The acetonitrile phase was washed with hexane and concentrated. The residue was washed with acetonitrile to obtain the title compound (0.4 mg).

LCMS: [M+H]⁺/Rt=323/0.489 min^(C)

Example 36: 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid

Phenylboronic acid (0.146 g) and 1 N hydrochloric acid/acetic acid solution (25.2 mL) were added to Reference Example (R)-36 (1.0 g). The reaction mixture was stirred for 1 hour at room temperature and then concentrated. The residue was dissolved in methanol (3 mL) and washed twice with heptane (6 mL) (the washing process removes the supernatant (top layer) after standing). The bottom layer was concentrated under reduced pressure, and the resulting residue was purified by reversed phase column chromatography to obtain the title compound (200 mg).

¹H-NMR (600 MHz, D₂O) δ: 7.56 (1H, m), 6.99 (1H, m), 6.73 (1H, d, J=8.4 Hz), 5.86 (1H, d, J=8.4 Hz), 4.86-4.65 (2H, m), 4.51-4.46 (0.5H, m), 4.30-4.14 (2H, m), 3.96-3.82 (1.5H, m), 2.45-2.43 (2H, m), 0.24-0.21 (2H, m).

LCMS: [M+H]⁺/Rt=387.05/0.421 min^(C)

Example 37: 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid Disodium Salt

Phenylboronic acid (2.46 mg), hexane (0.337 mL), and 4 N hydrochloric acid/cyclopentyl methyl ether solution (0.151 mL) were added to an acetonitrile (0.337 mL) solution of the compound of Reference Example (S)-36 (18.1 mg), and the reaction mixture was stirred for 16 hours at room temperature. After allowing it to stand, the supernatant (top layer) of the reaction solution separated into two layers was removed, and the remaining bottom layer was washed with hexane (the washing process removes the supernatant after standing). The solid produced in the solution at the bottom layer was washed with diethyl ether. The residue of the solid obtained by removing the solvent was dried under reduced pressure. The resulting dried residue was dissolved in water. An aqueous 2 N sodium hydroxide solution (0.1 mL) was added. The mixture was purified by reversed phase column chromatography to obtain the title compound (7.8 mg) as a white solid.

LCMS: [M+H]⁺/Rt=387.00/0.428 min^(C)

The column retention times of the compound of Example 36 and the compound of Example 37 in chiral chromatography were the following.

Column: CROWNPAK CR-I(−) (0.30 cm I.D.×15 cm L) (Daicel Corporation)

Mobile phase: aqueous perchloric acid solution (pH 1.0)/acetonitrile (60% perchloric acid: 1.7%)

Flow rate: 0.5 mL/min

Temperature: 25° C.

Rt of compound of Example 36: 6.001 min

Rt of compound of Example 37: 3.968 min

Optical purity of Example 36 (computed by HPLC area percentage value): 98.5% ee

Optical purity of Example 37 (computed by HPLC area percentage value): 98.3% ee

The stereostructure of the compound of Example 36 was estimated to be an R form by Mosher's method (reference document for Mosher's method include: The Journal of Organic Chemistry, 2016, 81, 7373).

Example 38: 8-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic Acid Disodium Salt

Phenylboronic acid (18.6 mg) and 4 N hydrochloric acid/cyclopentyl methyl ether solution (1.21 mL) were added to an acetic acid (1.61 mL) solution of the compound of Reference Example 37 (130 mg) while cooling with ice, and the reaction mixture was stirred for 3 hours at room temperature. The solvent was removed under reduced pressure. The resulting dried residue was dissolved in water. An aqueous 2 N sodium hydroxide solution (0.402 mL) was added, and the mixture was purified by reversed phase column chromatography to obtain the title compound (5 mg) as a white solid.

LCMS: [M+H]⁺/Rt=401.31/0.473 min^(C)

Example 39: 2-hydroxy-7-{[1-(4H-1,2,4-triazole-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Trifluoroacetate

Phenylboronic acid (35.6 mg), hexane (2.9 mL), and TFA (2.23 mL) were added to an acetonitrile (2.9 mL) solution of the compound of Reference Example 41 (205 mg), and the reaction mixture was stirred for 5 hours at room temperature. After allowing it to stand, the supernatant (top layer) of the reaction solution separated into two layers was removed, and the remaining bottom layer was washed with hexane (the washing process removes the supernatant after standing). The solid produced in the solution at the bottom layer was washed with diethyl ether. The residue of the solid obtained by removing the solvent was dried under reduced pressure. The resulting dried residue was purified by reversed phase column chromatography to obtain the title compound (39.8 mg) as a colorless solid.

¹H-NMR (CD₃OD) δ: 8.69 (1H, s), 7.11 (1H, d, J=8.1 Hz), 6.21 (1H, d, J=8.1 Hz), 4.95-4.85 (1H, m), 4.44-4.35 (2H, m), 4.04-3.99 (2H, m), 2.65 (2H, t, J=8.1 Hz), 1.04 (2H, t, J=8.1 Hz).

LCMS: [M+H]⁺/Rt=395.1/1.24 min^(B)

Example 40: 7-({1-[2-amino-2-(1H-imidazol-4-yl)(2H)ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Dihydrochloride

Acetic acid-d1 (3 mL) was added to the compound of Reference Example 36-4 (0.3 g, 0.377 mmol), and the reaction mixture was stirred for 4 days at room temperature. Phenylboronic acid (46 mg, 0.377 mmol) and 4 N hydrochloric acid cyclopentyl methyl ether solution (2 mL, 8.0 mmol) were then added, and the reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was dried and solidified under reduced pressure. The resulting dried residue was dissolved in methanol (1 mL), and isopropanol (10 mL) was added. The precipitated solid was filtered out, dried and solidified under reduced pressure. The resulting solid was purified by reversed phase column chromatography, and the resulting dried residue was washed with acetonitrile, dried and solidified under reduced pressure to obtain the title compound (71 mg) as a white solid.

¹H-NMR (0.1M Na₂CO₃ in D₂O) δ: 7.84-7.76 (1H, n), 7.30-7.20 (1H, n), 6.91-6.89 (1H, m), 6.12-6.01 (1H, n), 5.02-4.89 (1H, m), 4.58-3.76 (4H, m), 2.59 (2H, n), 0.55 (2H, m).

LCMS: [M+H]⁺/Rt=388.12/0.410 min^(C)

Example 41: 7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

A reaction, work-up, and purification were performed using the compound of Reference Example 39 (153 mg, 0.189 mmol) as the starting material by the same method described in Example 36 to obtain the title compound (42 mg) as a white solid.

¹H-NMR (0.1M Na₂CO₃ in D₂O) δ: 7.77 (1H, m), 7.18 (1H, m), 6.83 (1H, m), 5.91 (1H, m), 4.35 (1H, m), 3.95-4.20 (2H, m), 3.30-3.51 (2H, m), 2.57 (2H, m), 1.63 (3H, s), 0.36 (2H, m).

LCMS: [M+H]⁺/Rt=401.12/0.422 min^(C)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 56 and 58 as the starting materials by the same method described in Example 37 to obtain Example compounds 42 and 43, respectively. However, if hydrochloride is the final product (Example 43), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-5 Starting Example material Structural formula NMR and/or LCMS 42 Reference Example 56

LCMS: [M + H]⁺/Rt = 401.10/0.451 min^(C) 43 Reference Example 58

LCMS: [M + H]⁺/Rt = 399.10/0.493 min^(C) ¹H-NMR (CD₃OD) δ: 8.61 (1H, s), 7.21 (1H, s), 7.17 (1H, d, J = 7.9 Hz), 6.34 (1H, d, J = 7.9 Hz). 5.18- 5.15 (1H, m), 4.70-4.67 (2H, m), 4.34- 4.21 (2H, m), 2.70 (2H, t, J = 7.6 Hz), 2.67 (3H, s), 1.05 (2H, t, J = 7.6 Hz).

The names of the compounds of Examples 42 and 43 are described below.

8-({(3S)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic Acid Disodium Salt (Example 42) 2-hydroxy-7-{[1-(4-hydroxy-6-methylpyridine-3-carbonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride (Example

43)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 38, 48, 49, 55, 57, 63, 64, and 71 as the starting materials by the same method described in Example 38 to obtain each of the following Example compounds 44 to 51. However, if hydrochloride is the final product (Examples 46 and 51), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-6 Starting Example material Structural formula NMR and/or LCMS 44 Reference Example 57

LCMS: [M + H]⁺/Rt = 401.20/0.393 min^(C) 45 Reference Example 48

LCMS: [M + H ]⁺/Rt = 445.2/0.82 min^(B) ¹H-NMR (CD₃OD) δ: 7.57 (1H, s), 7.08 (1H, s), 6.70 (1H, d, J = 8.1 Hz), 5.90 (1H, d, J = 8.1 Hz), 4.98-4.90 (1H, m), 4.62-3.93 (7H, m), 2.55 (2H, t, J = 5.4 Hz), 0.44 (2H, t, J = 5.4 Hz). 46 Reference Example 49

LCMS: [ M + H ]⁺/Rt = 444.3/0.52 min^(B) ¹H-NMR (CD₃OD) δ: 9.01 (1H, s), 7.88 (1H, s), 7.15 (1H, d, J = 8.1 Hz), 6.35- 6.28 (1H, m), 5.55 (1H, d, J = 16.2 Hz), 5.20-4.97 (3H, m), 4.77-3.72 (4H, m), 2.69 (2H, t, J = 8.1 Hz), 1.05 (2H, t, J = 8.1 Hz). 47 Reference Example 63

LCMS: [M + H]⁺/Rt = 398.3/0.82 min^(B) ¹H-NMR (CD₃OD) δ: 8.59 (1H, s), 8.50-8.47 (1H, m), 7.90-7.84 (1H, m), 7.47-7.41 (1H, m), 6.67 (1H, d, J = 8.1 Hz), 5.89-5.85 (1H, m), 5.01-4.94 (1H, m), 4.73-3.73 (5H, m), 2.54 (2H, t, J = 5.4 Hz), 0.41 (2H, t, J = 5.4 Hz).

TABLE 3-7 48 Reference Example 64

LCMS: [M + H]⁺/Rt = 401.3/0.92 min^(B) ¹H-NMR (CD₃OD) δ: 7.61-7.59 (1H, m), 7.47 (1H, s), 6.68 (1H, d, J = 8.1 Hz), 5.90-5.86 (1H, s), 5.00-4.94 (1H, m), 4.64-3.96 (5H, m), 3.86 (3H, s), 2.55 (2H, t, J = 8.1 Hz), 0.41 (2H, t, J = 8.1 Hz). 49 Reference Example 55

LCMS: [M + H]⁺/Rt = 401.05/0.442 min^(C) 50 Reference Example 38

LCMS: [M + H]⁺/RT = 401.16/0.387 min^(C) ¹H-NMR (D₂O) δ: 6.62 (1H, d, J = 12.8 Hz), 6.48 (1H, d, J = 7.9 Hz), 5.61 (1H, d, J = 7.9 Hz), 4.61-4.49 (2H, m), 4.30-4.26 (1H, m), 4.05-3.94 (1H, m), 3.90-3.81 (1H, m), 3.70-3.63 (1H, m), 2.18 (2H, t, J = 6.4 Hz), 1.94 (3H, d, J = 4.3 Hz), 0.00 (2H, t, J = 6.1 Hz). 51 Reference Example 71

LCMS: [M + H]⁺/Rt = 404.2/0.95 min^(B) ¹H-NMR (CD₃OD) δ: 9.13-9.10 (1H, m), 7.92-7.91 (1H, m), 7.13 (1H, d, J = 8.2 Hz), 6.27 (1H, d, J = 8.2 Hz), 5.50- 5.49 (1H, m), 5.12-5.03 (1H, m), 4.73- 3.62 (4H, m), 2.68 (2H, t, J = 8.1 Hz), 1.05 (2H, t, J = 8.1 Hz).

The names of the compounds of Examples 44 to 51 are described below.

-   8-({1-[amino(1-methyl-1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 44) -   8-[(1-{amino[1-(carboxymethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid trisodium salt (Example 45) -   7-[(1-{amino[1-(2-amino-2-oxoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 46) -   8-({1-[amino(pyridin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 47) -   8-({1-[amino(1-methyl-1H-pyrazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 48) -   8-({(3R)-1-[amino(1H-imidazol-4-yl)acetyl]pyrrolidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 49) -   8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 50) -   7-({1-[amino(1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 51)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 106 to 108 as the starting materials by the same method described in Example 38 to obtain the following Example compounds 52 to 54, respectively.

TABLE 3-8 Starting Example material Structural formula NMR and/or LCMS 52 Reference Example 106

LCMS: [M + H]⁺/Rt = 394.4/1.20 min^(B) ¹H-NMR (CD₃OD) δ: 8.07 (1H, s), 7.87 (1H, s), 7.12 (1H, d, J = 8.1 Hz), 6.23 (1H, d, J = 8.1 Hz), 4.93-4.87 (1H, m), 4.34-4.26 (2H, m), 3.91-3.88 (2H, m), 2.66 (2H, t, J = 8.1 Hz), 1.04 (2H, t, J = 8.1 Hz). 53 Reference Example 107

LCMS: [M + H]⁺/Rt = 405.3/1.41 min^(B) ¹H-NMR (CD₃OD) δ: 9.00 (1H, s), 8.87 (1H, d, J = 5.4 Hz), 8.31 (1H, d, J = 8.1 Hz), 7.74-7.00 (1H, m), 7.10 (1H, d, J = 8.1 Hz), 6.22 (1H, d, J = 8.1 Hz), 4.97-4.65 (1H, m), 4.33-4.27 (2H, m), 3.83-3.77 (2H, m), 2.65 (2H, t, J = 8.1 Hz), 1.02 (2H, t, J = 8.1 Hz). 54 Reference Example 108

LCMS: [M + H]⁺/Rt = 421.3/1.30 min^(B) ¹H-NMR (CD₃OD) δ: 8.46-8.36 (1H, m), 8.06 (1H, dd, J = 5.4 Hz, 2.7 Hz), 7.70-7.57 (2H, m), 7.12 (1H, d, J = 8.1 Hz), 6.28 (1H, d, J = 8.1 Hz), 5.08- 5.00 (1H, m), 4.61-4.55 (2H, m), 4.33- 4.26 (2H, m), 2.65 (2H, t, J = 8.1 Hz), 1.05 (2H, t, J = 8.1 Hz).

The names of the compounds of Examples 52 to 54 are described below.

-   2-hydroxy-7-{[1-(1H-imidazole-4-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 52) -   2-hydroxy-7-{[1-(pyridine-3-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 53) -   2-hydroxy-7-{[1-(1-oxo-1λ⁵-pyridine-2-sulfonyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 54)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 40, 43 to 47, 50, 51, 59, 65, 66, 69, 70, 114 to 116, and 127 as the starting materials by the same method described in Example 4 to obtain the following Example compounds 55 to 71 (corresponding starting materials are not in order) However, if a tree form is the final product (Examples 57, 61, 64, 65, 67, and 71), the free form was obtained from purifying the compound without sodium hydroxide treatment. If hydrochloride is the final product (Examples 58, 62, and 63), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-9 Starting Example material Structural formula NMR and/or LCMS 55 Reference Example 65

LCMS: [M + H]⁺/Rt = 404.4/1.03 min^(B) ¹H-NMR (CD₃OD) δ: 6.69 (1H, d, J = 8.2 Hz), 6.31 (1H, s), 5.90 (1H, d, J = 8.2 Hz), 5.00-4.86 (1H, m), 4.63-4.47 (1H, m), 4.39-4.21 (2H, m), 4.08-3.96 (1H, m), 3.41-3.35 (2H, m), 2.63-2.49 (2H, m), 0.48-0.35 (2H, m). 56 Reference Example 66

LCMS: [M + H]+/Rt = 390.2/1.16 min^(B) ¹H-NMR (CD₃OD) δ: 7.24 (1H, s), 6.72 (1H, d, J = 8.1 Hz), 5.94 (1H, d, J = 8.1 Hz), 4.95-4.90 (2H, m), 4.62-4.56 (1H, m), 4.47-4.41 (1H, m), 4.16-4.12 (1H, m), 2.59-2.54 (2H, m), 0.47-0.42 (2H, m). 57 Reference Example 69

LCMS: [M + H]⁺/Rt = 373.22/1.62 min^(D) ¹H-NMR (CD₃OD) δ: 8.11 (1H, d, J = 1.1 Hz), 7.91 (1H, s), 7.22-7.13 (1H, m), 6.40-6.28 (1H, m), 5.32 (2H, s), 5.16-5.10 (1H, m), 4.74-4.66 (1H, m), 4.50-4.42 (1H, m), 4.37-4.31 (1H, m), 4.10-4.02 (1H, m), 2.77-2.62 (2H, m), 1.10-1.01 (2H, m).

TABLE 3-10 58 Reference Example  70

LCMS: [M + H]⁺/Rt = 415.2/0.52 min^(B) ¹H-NMR (CD₃OD) δ: 9.04 (1H, s), 7.63 (1H, s), 7.18 (1H, d, J = 8.1 Hz), 6.37 (1H, d, J = 8.1 Hz), 5.15-5.12 (1H, m), 4.79-4.73 (1H, m), 4.60 (2H, t, J = 5.4 Hz), 4.54-4.33 (2H, m), 4.18-4.02 (1H, m), 3.79 (2H, s), 3.53 (2H, t, J = 5.4 Hz), 2.71-2.65 (2H, m), 1.10-1.04 (2H, m). 59 Reference Example  40

LCMS: [M + H]⁺/Rt = 358.2/0.90 min^(B) ¹H-NMR (CD₃OD) δ: 7.81 (1H, s), 7.67 (1H, s), 6.93 (1H, d, J = 8.1 Hz), 6.11 (1H, d, J = 8.1 Hz), 5.14-5.03 (1H, m), 4.92-4.73 (1H, m), 4.59-4.52 (2H, m), 4.24-4.19 (1H, m), 2.60 (2H, t, J = 8.1 Hz), 0.40 (2H, t, J = 8.1 Hz). 60 Reference Example 127

LCMS: [M + H]⁺/Rt = 358.1/1.17 min^(B) ¹H-NMR (CD₃OD) δ: 7.28 (2H, s), 6.93 (1H, d, J = 8.1 Hz), 6.11 (1H, d, J = 8.1 Hz), 5.16-5.09 (1H, m), 5.04-4.71 (1H, m), 4.67-4.55 (2H, m), 4.27-4.21 (1H, m), 2.61 (2H, t, J = 8.1 Hz), 0.41 (2H, t, J = 8.1 Hz). 61 Reference Example  43

LCMS: [M + H]⁺/Rt = 403.17/1.58 min^(D) ¹H-NMR (CD₃OD) δ: 8.06 (1H, s), 7.21-7.12 (1H, m), 6.41-6.27 (1H, m), 5.31 (2H, s), 5.16-5.10 (1H, m), 4.77-4.67 (3H, m), 4.50-4.42 (1H, m), 4.38-4.31 (1H, m), 4.10-4.02 (1H, m), 2.74-2.63 (2H, m), 1.06 (2H, t, J = 7.7 Hz). 62 Reference Example 114

LCMS: [M + H]⁺/Rt = 416.30/1.25 min^(D) ¹H-NMR (CD₃OD) δ: 8.12 (1H, s), 7.23-7.10 (1H, m), 6.41-6.29 (1H, m), 5.30 (2H, s), 5.18-5.10 (1H, m), 4.78-4.71 (1H, m), 4.50-4.43 (1H, m), 4.40-4.28 (3H, m), 4.11-4.03 (1H, m), 2.79-2.65 (5H, m), 1.10-1.02 (2H, m). 63 Reference Example 115

LCMS: [M + H]⁺/Rt = 471.27/1.15 min^(D) ¹H-NMR (CD₃OD) δ: 8.29 (1H, s), 7.21-7.13 (1H, m), 6.40-6.30 (1H, m), 5.34 (2H, s), 5.19-5.13 (1H, m), 4.79-4.73 (1H, m), 4.64 (2H, s), 4.50-4.45 (1H, m), 4.41-4.36 (1H, m), 4.11-4.04 (1H, m), 3.71-3.54 (8H, m), 2.74-2.66 (2H, m), 1.10-1.03 (2H, m).

TABLE 3-11 64 Reference Example 116

LCMS: [M + H]⁺/Rt = 417.26/1.56 min^(D) ¹H-NMR (CD₃OD) δ: 8.10 (1H, s), 7.23-7.13 (1H, m), 6.43-6.28 (1H, m), 5.36 (2H, s), 5.19-5.12 (1H, m), 4.76-4.68 (1H, m), 4.52-4.44 (1H, m), 4.38-4.32 (1H, m), 4.13-4.06 (1H, m), 3.90-3.78 (2H, m), 3.04-2.95 (2H, m), 2.78-2.65 (2H, m), 1.12-1.00 (2H, m). 65 Reference Example  44

LCMS: [M + H]⁺/Rt = 403.35/1.44 min^(D) ¹H-NMR (CD₃OD) δ: 7.77 (1H, s), 7.23-7.12 (1H, m), 6.44-6.25 (1H, m), 5.35-5.31 (2H, m), 5.16-5.12 (1H, m), 4.76-4.70 (3H, m), 4.51-4.44 (1H, m), 4.40-4.32 (1H, m), 4.11-4.04 (1H, m), 2.77-2.65 (2H, m), 1.10-1.03 (2H, m). 66 Reference Example  45

LCMS: [M + H]⁺/Rt = 416.34/1.12 min^(D) ¹H-NMR (D₂O) δ: 7.76 (1H, s), 6.89 (1H, d, J = 8.0 Hz), 6.06 (1H, d, J = 8.0 Hz), 5.33-5.22 (2H, m), 5.12-5.06 (1H, m), 4.74-4.67 (1H, m), 4.49-4.36 (2H, m), 4.16-4.10 (1H, m), 3.79 (2H, s), 2.62-2.54 (2H, m), 2.34 (3H, s), 0.41-0.33 (2H, m). 67 Reference Example  59

LCMS: [M + H]⁺/Rt = 373.35/1.59 min^(D) ¹H-NMR (CD₃OD) δ: 8.19 (1H, s), 7.21-7.07 (1H, m), 6.42-6.21 (1H, m), 5.09-5.05 (1H, m), 4.72-4.65 (1H, m), 4.43-4.36 (1H, m), 4.35-4.28 (1H, m), 4.03-3.95 (1H, m), 3.84 (2H, s), 2.71-2.61 (2H, m), 1.06-0.97 (2H, m). 68 Reference Example  46

LCMS: [M + H]⁺/Rt = 431.12/1.71 min^(D) ¹H-NMR (D₂O) δ: 7.84 (1H, d, J = 6.9 Hz), 6.92 (1H, d, J = 8.0 Hz), 6.09 (1H, d, J = 8.0 Hz), 5.33-5.22 (2H, m), 5.12-5.05 (1H, m), 4.72-4.66 (1H, m), 4.50-4.43 (1H, m), 4.43-4.37 (1H, m), 4.16-4.10 (1H, m), 3.64 (2H, s), 2.64-2.56 (2H, m), 0.51-0.42 (2H, m). 69 Reference Example  47

LCMS: [M + H]⁺/Rt = 431.16/1.44 min^(D) ¹H-NMR (D₂O) δ: 7.86 (1H, s), 6.89 (1H, d, J = 8.0 Hz), 6.06 (1H, d, J = 8.0 Hz), 5.06-5.00 (3H, m), 4.70-4.65 (1H, m), 4.44-4.35 (2H, m), 4.11-4.05 (1H, m), 3.80-3.67 (2H, m), 2.62-2.55 (2H, m), 0.41-0.34 (2H, m). 70 Reference Example  50

LCMS: [M + H]⁺/R = 388.35/0.93 min^(D) ¹H-NMR (D₂O) δ: 7.77-7.72 (1H, m), 6.92-6.34 (1H, m), 6.05-5.93 (1H, m), 5.03-4.85 (2H, m), 4.64-3.91 (4H, m), 2.62-2.49 (2H, m), 0.49-0.37 (2H, m).

TABLE 3-12 71 Reference Example 51

LCMS: [M + H]⁺/R = 418.13/2.03 min^(D) ¹H-NMR (CD₃OD) δ: 8.92 (1H, s), 7.22-7.13 (1H, m), 6.40-6.12 (1H, m), 5.41-5.34 (2H, m), 5.19-5.12 (1H, m), 4.78-4.71 (1H, m), 4.52-4.45 (1H, m), 4.44-4.37 (1H, m), 4.13-4.06 (1H, m), 2.76-2.66 (2H, m), 1.11-1.02 (2H, m).

The names of the compounds of Examples 55 to 71 are described below.

-   8-({1-[(2-amino-1,3-thiazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 55) -   8-{[1-(2-amino-1,3-thiazole-4-carbonyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 56) -   2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 57) -   7-[(1-{[1-(2-aminoethyl)-1H-imidazol-4-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 58) -   4,4-dihydroxy-8-{[1-(1H-imidazole-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 59) -   4,4-dihydroxy-8-{[1-(1H-imidazole-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 60) -   2-hydroxy-7-[(1-{[4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 61) -   2-hydroxy-7-{[1-({4-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 62) -   2-hydroxy-7-{[1-({4-[(piperazin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid dihydrochloride (Example 63) -   2-hydroxy-7-[(1-{[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 64) -   2-hydroxy-7-[(1-{[5-(hydroxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 65) -   4,4-dihydroxy-8-{[1-({5-[(methylamino)methyl]-1H-1,2,3-triazol-1-yl}acetyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 66) -   2-hydroxy-7-({1-[(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 67) -   8-[(1-{[4-(carboxymethyl)-1H-1,2,3-triazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid trisodium salt (Example 68) -   8-[(1-{[1-(carboxymethyl)-1H-1,2,3-triazol-4-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid trisodium salt (Example 69) -   8-({1-[amino(1H-1,2,3-triazol-4-yl)acetyl]azetidin-3-yl}oxy-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 70) -   2-hydroxy-7-({1-[(4-nitro-1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 71)

Example 72: 7-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride

Example 72-1: Tert-butyl 6-[(1-{[(tert-butoxycarbonyl)amino](3,4-dihydroxyphenyl)acetyl}azetidin-3-yl)oxy]-2-[(tert-butoxycarbonyl)oxy]-3-{2-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-2H-4,6-methano-1,3,2-benzodioxaborol-2-yl]ethyl}benzoate

Palladium on carbon (19 mg, Pd content: 10%, wetted with ca. 55% water) was added to a methanol solution (2 mL) of the compound of Reference Example 67 (190 mg, 0.187 mmol), and the reaction mixture was stirred for 2.5 hours under a hydrogen atmosphere at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methanol, and the combined filtrate was concentrated to obtain the title compound (143 mg) as a colorless amorphous compound.

¹H-NMR (CDCl₃) δ: 7.19 (1H, d, J=8.1 Hz), 6.93 (1H, d, J=16.2 Hz), 6.82-6.71 (2H, m), 6.32 (1H, d, J=8.1 Hz), 5.99 (1H, br), 5.77-5.65 (1H, m), 5.08-3.80 (7H, m), 2.63-2.56 (2H, m), 2.36-2.27 (1H, m), 2.19-2.12 (1H, m), 2.04-1.99 (1H, m), 1.89-1.77 (2H, m), 1.63-1.39 (27H, m), 1.35 (3H, s), 1.28 (3H, s), 1.12-1.00 (3H, m), 0.83 (3H, s)

LCMS: [M+H]⁺/Rt=837.7/2.83 min^(B)

Example 72: 7-({1-[amino(3,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride

Phenylboronic acid (18.7 mg, 0.153 mmol), hexane (1.5 mL), and 4 N hydrochloric acid/dioxane solution (0.76 mL) were added to an acetonitrile solution (1.5 mL) of the compound of Example 72-1 (128 mg, 0.153 mmol), and the reaction mixture was stirred for 17 hours at room temperature. The reaction solution was allowed to stand. The supernatant (top layer) was removed, and hexane (5 mL) was added to the remaining bottom layer. After stirring and then allowing it to stand, the supernatant was removed. This was repeated 5 times. Diethyl ether (5 mL) was added to the bottom layer. After stirring and then allowing it to stand, the supernatant (top layer) was removed. This was repeated 3 times. The resulting residue was dried under reduced pressure. Since an intermediate (Boc-undeprotected form of the title compound) was also found in the resulting residue, a 4 N hydrochloric acid/dioxane solution (3.0 mL) was further added. The reaction mixture was stirred for 21 hours at room temperature, and the reaction solution was concentrated. The resulting residue was dissolved in methanol (1.5 mL) and purified by reversed phase column chromatography to obtain the title compound (19.3 mg) as a light yellow solid.

¹H-NMR (CD₃OD) δ: 7.25-7.05 (1H, in), 6.91-6.79 (3H, m), 6.25-6.00 (1H, m), 5.09-4.94 (1H, m), 4.63-3.98 (3H, m), 3.76-3.53 (2H, m), 2.81-2.39 (2H, m), 1.16-0.51 (2H, m).

LCMS: [M+H]⁺/Rt=429.2/0.96 min

Example 73: 7-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride

Example 73-1: 7-[(1-{amino[2,4-bis(benzyloxy)phenyl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid

A reaction, work-up, and purification were performed using the compound of Reference Example 68 (195 mg, 0.192 mmol) as the starting material by the same method described in Example 72 to obtain the title compound (78 mg) as a colorless solid.

¹H-NMR (CD₃OD) δ: 7.45-7.26 (11H, m), 7.14-7.11 (1H, m), 6.87-6.79 (1H, m), 6.74-6.65 (1H, m), 6.16 (1H, brs), 5.25-5.04 (5H, m), 5.03-4.91 (1H, m), 4.48-3.90 (3H, m), 3.77-3.60 (1H, m), 2.73-2.64 (2H, m), 1.09-1.02 (2H, m).

LCMS: [M+H]⁺/Rt=609.6/1.80 min^(B)

Example 73: 7-({1-[amino(2,4-dihydroxyphenyl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid Hydrochloride

Palladium on carbon (13 mg, Pd content: 10%, wetted with ca. 55% water) was added to a THF solution (25 mL) of the compound of Example 73-1 (65.1 mg, 0.101 mmol), and the reaction mixture was stirred for 2.5 hours under a hydrogen atmosphere at room temperature. Subsequently, methanol (0.25 mL) was added, and the reaction mixture was stirred for 4 days at room temperature. Subsequently, palladium on carbon (13 mg) was added, and the reaction mixture was stirred for 1 day at room temperature. Palladium on carbon (13 mg) was further added, and the reaction mixture was stirred for 5 days at room temperature. The reaction solution was filtered through cellulose. The filtered substance was washed with methanol, and the combined filtrate was concentrated. The resulting residue was dissolved in methanol (2 mL) and purified by reversed phase column chromatography to obtain the title compound (9.0 mg) as a colorless solid.

¹H-NMR (CD₃OD) δ: 7.13-5.98 (5H, m), 5.23-5.19 (1H, m), 5.04-4.79 (1H, m), 4.51-3.47 (4H, m), 2.85-1.93 (2H, m), 1.16-0.65 (2H, m).

LCMS: [M+H]⁺/Rt=429.2/0.94 min^(B)

Example 74: 7-{[1-(S-benzyl-D-cysteinyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine 8-carboxylic acid trifluoroacetate

Trifluoroacetic acid 3.3 mL was added to the compound of Reference Example 72 (106 mg), and the reaction mixture was stirred for 8 hours at room temperature. The reaction mixture was dried and solidified under reduced pressure. The resulting dried residue was purified by reversed phase column chromatography. The resulting dried residue was washed with acetonitrile, dried and solidified under reduced pressure to obtain the title compound (24.6 mg) as a white solid.

LCMS: [M+H]⁺/Rt=865.61/1.332 min^(A)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 73 and 74 as the starting materials by the same method described in Reference Example 74 to obtain the following Example compounds 75 and 76, respectively.

TABLE 3-13 Starting Example material Structural formula NMR and/or LCMS 75 Reference Example 73

LCMS: M + H]⁺/Rt = 367.09/0.495 min^(C) ¹H-NMR (400 MHz, CD₃OD) δ: 7.19-7.11 (1H, m), 6.16-6.12 (1H, m), 5.07-5.02 (2H, m), 4.53-4.33 (2H, m), 4.23-4.06 (2H, m), 3.07-2.99 (1H, m), 2.89-2.82 (1H, m), 2.76-2.68 (1H, m), 2.62-2.50 (1H, m), 1.07-0.67 (2H, m). 76 Reference Example 74

LCMS: M + H]⁺/Rt = 395.17/0.489 min^(C) ¹H-NMR (400 MHz, CD₃OD) δ: 7.19-7.12 (1H, m), 6.37-6.13 (1H, m), 5.06-5-01 (2H, m), 4-77-4.73 (1H, m), 4.52-4.39 (2H, m), 4.18-3.99 (2H, m), 2.76-2.53 (2H, m), 1.54 (3H, s), 1.46 (3H, s), 1.08-0.68 (2H, m).

The names of the compounds of Examples 75 and 76 are described below.

-   7-[(1-D-cysteinylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 75) -   2-hydroxy-7-{[1-(3-sulfanyl-D-valyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 76)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 42, 52, 76 to 78, and 109 to 113 as the starting materials by the same method described in Example 38 to obtain the following Example compounds 77 to 86 (corresponding starting materials are not in order). However, if a free form is the final product (Example 83), the free form was obtained from purifying the compound without sodium hydroxide treatment. If hydrochloride is the final product (Examples 79, 80, 82, and 84 to 86), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-14 Starting Example material Structural formula NMR and/or LCMS 77 Reference Example  76

LCMS: [M + H]⁺/Rt = 379.1/0.76 min^(B) ¹H-NMR (CD₃OD) δ: 6.71 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.00-4.93 (1H, m), 4.73-4.61 (1H, m), 4.37-4.27 (2H, m), 4.05-4.01 (1H, m), 3.79-3.71 (1H, m), 2.59-2.47 (3H, m), 2.38-2.25 (1H, m), 0.41 (2H, t, J = 8.1 Hz). 78 Reference Example  77

LCMS: [M + H]⁺/Rt = 406.3/1.00 min^(B) ¹H-NMR (CD₃OD) δ: 6.73 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5 05-4-95 (1H, m), 4-75-4.53 (1H, m), 4.48-4.28 (3H, m), 4.08-3.98 (1H, m), 3.66-3.42 (1H, m), 2.57 (2H, d, J = 8.1 Hz), 1.32-1.25 (6H, m), 0.45 (2H, t, J = 8.1 Hz). 79 Reference Example  42

LCMS: [M + H]⁺/Rt = 378.2/0.81 min^(B) ¹H-NMR (CD₃OD) δ: 7.21-7.11 (1H, m), 6.38-6.10 (1H, m), 5.16-4.98 (1H, m), 4.78-4.64 (1H, m), 4.54-4.26 (3H, m), 4.12-4.02 (1H, m), 2.90-2.54 (4H, m), 1.10-0.64 (2H, m). 80 Reference Example 109

LCMS: [M + H]⁺/Rt = 378.2/0.58 min^(B) ¹H-NMR (CD₃OD) δ: 7.18 (1H, d, J = 8.1 Hz), 6.35 (1H, d, J = 8.1 Hz), 5.17-5.07 (1H, m), 4.79-4.72 (1H, m), 4.55-4.27 (3H, m), 4.12-4.01 (1H, m), 2.92-2.64 (4H, m), 1.07 (2H, t, J = 8.1 Hz). 81 Reference Example  78

LCMS: [M + H]⁺/Rt = 379.1/0.56 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.94 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.73-4.61 (1H, m), 4.37-4.27 (2H, m), 4.06-4.00 (1H, m), 3.80-3.72 (1H, m), 2.59-2.47 (3H, m), 2.39-2.26 (1H, m), 0.44 (2H, t, J = 8.1 Hz). 82 Reference Example  52

LCMS: [M + H]⁺/Rt = 351.0/0.48 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.2 Hz), 6.35 (1H, d, J = 8.1 Hz), 5.18-5.09 (1H, m), 4.79-4.70 (1H, m), 4.55-4.33 (2H, m), 4.12-4.02 (2H, m), 3.92-3.84 (1H, m), 3.80-3.73 (1H, m), 2.70 (2H, t, J = 8.1 Hz), 1.06 (2H, t, J = 8.1 Hz).

TABLE 3-15 83 Reference Example 110

LCMS: [M + H]⁺/Rt = 363.0/0.97 min^(B) ¹H-NMR (CD₃OD) δ: 7.18-7.09 (1H, m), 6.33-6.09 (1H, m), 5.10-5.02 (1H, m), 4.67-4.62 (1H, m), 4.40-4.34 (1H, m), 4.28-4.23 (1H, m), 3.99-3.94 (1H, m), 2.72-2.38 (6H, m), 1.09-0.91 (2H, m). 84 Reference Example 111

LCMS: [M + H]⁺/Rt = 392.1/0.79 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.2 Hz), 6.40-6.30 (1H, m), 5.17-5.08 (1H, m), 4.77-4.71 (1H, m), 4.54-4.31 (2H, m), 4.14-4.02 (2H, m), 2.70 (2H, t, J = 8.1 Hz), 2.48-2.42 (2H, m), 2.15-2.00 (2H, m), 1.06 (2H, t, J = 8.1 Hz). 85 Reference Example 113

LCMS: [M + H]⁺/Rt = 393.1/0.47 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.2 Hz), 6.35 (1H, d, J = 8.2 Hz), 5.17-5.08 (1H, m), 4.81-4.72 (1H, m), 4.55-4.30 (2H, m), 4.17-4.03 (2H, m), 3.60-3.40 (2H, m), 2.70 (2H, t, J = 8.1 Hz), 1.06 (2H, t, J = 8.1 Hz). 86 Reference Example 112

LCMS: [M + H]⁺/Rt = 392.1/0.86 min^(B) ¹H-NMR (CD₃OD) δ: 7.18 (1H, d, J = 8.2 Hz), 6.39-6.30 (1H, m), 5.18-5.09 (1H, m), 4.80-4.72 (1H, m), 4.55-4.32 (2H, m), 4.21-4.03 (2H, m), 3.60-3.42 (2H, m), 2.70 (2H, t, J = 8.1 Hz), 2.01-1.98 (3H, m), 1.06 (2H, t, J = 8.1 Hz).

The names of the compounds of Examples 77 to 86 are described below.

-   8-({1-[(23)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid trisodium salt (Example 77) -   8-{[1-(D-alanyl-D-alanyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 78) -   7-[(l-L-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 79) -   7-[(1-D-asparaginylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 80) -   8-({1-[(2R)-2-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid trisodium salt (Example 81) -   2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 82) -   7-{[1-(4-amino-4-oxobutanoyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 83) -   7-[(1-D-glutaminylazetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 84) -   7-({1-[3-(carbamoylamino)-D-alanyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 85) -   1-(3-acetamido-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 86)

The following Example compounds 87 to 89 (corresponding starting materials are not in order) were obtained by performing a reaction and work-up using the compounds of Reference Examples 53, 54, and 75 as the starting materials by the same method described in Example 4, and purifying the compounds by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-16 Starting Example material Structural formula NMR and/or LCMS 87 Reference Example 54

LCMS: [M + H]+/Rt = 406.36/1.38 min^(D) ¹H-NMR (CD₃OD) δ: 7.22-7.12 (1H, m), 6.41-6.28 (1H, m), 5.17-5.07 (1H, m), 4.83-4.68 (1H, m), 4.54-4.24 (3H, m), 4.13-4.00 (1H, m), 3.11-2.77 (8H, m), 2.75-2.64 (21-I, m), 1.10-1.00 (2H, m). 88 Reference Example 53

LCMS: [M + H]+/Rt = 392.19/1.43 min^(D) ¹H-NMR (CD₃OD) δ: 7-24-7.10 (1H, m), 6.46-6.23 (1H, m), 5.18-5.09 (1H, m), 4.79-4.68 (1H, m), 4.57-4.27 (3H, m), 4.22-3.98 (1H, m), 2.85-2.61 (7H, m), 1.10-1.03 (2H, m). 89 Reference Example 75

LCMS: [M + H]+/Rt = 351.21/0.97 min^(D) ¹H-NMR (CD₃OD) δ: 7.20-7.14 (1H, m), 6.40-6.28 (1H, m), 5.17-5.09 (1H, m), 4.78-4.70 (1H, m), 4.56-4.41 (1H, m), 4.39-4.32 (1H, m), 4.14-4.02 (2H, m), 3.92-3.85 (1H, m), 3.81-3.74 (1H, m), 2.75-2.65 (2H, m), 1.12-1.03 (2H, m).

The names of the compounds of Examples 87 to 89 are described below.

-   7-{[1-(N,N-dimethyl-D-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 87) -   2-hydroxy-7-{[1-(N-methyl-D-asparaginyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 88) -   2-hydroxy-7-[(1-L-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborine-8-carboxylic     acid hydrochloride

Example 89

A reaction, work-up, and purification were performed using the compounds of Reference Examples 60, 62, 79 to 81, 124, and 125 as the starting materials by the same method described in Example 37 to obtain the following Example compounds 90 to 96 (corresponding starting materials are not in order). However, if a free form is the final product (Example 91), the free form was obtained from purifying the compound without sodium hydroxide treatment. If hydrochloride is the final product (Examples 90, 92, and 93), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-17 Exam- Starting ple material Structural formula NMR and/or LCMS 90 Reference Example  79

LCMS: [M + H]+/Rt = 377.4/0.425 min^(C) ¹H-NMR (CD₃OD) δ: 7.16 (1H, d, J = 8.5 Hz), 6.34 (1H, d, J = 8.5 Hz), 5.15 (1H, s), 4.72-4.66 (1H, m), 4.54-4.48 (4H, m), 4.32-4.25 (1H, m), 4.13-4.05 (1H, m), 3.39-3.33 (1H, m), 2.72-2.67 (2H, m), 2.61-2.57 (1H, m), 2.09-2.05 (1H, m), 1.03-1.00 (2H, m). 91 Reference Example  80

LCMS: [M + H]+/Rt = 429.1/0.537 min^(C) ¹H-NMR (CD₃OD) δ: 7.19-7.17 (1H, m), 636-6.33 (1H, m), 5.22-5-11 (2H, m), 4.58-4.50 (2H, m), 4.36-4.33 (1H, m), 4.13-4.11 (1H, m), 3.68-3.66 (1H, m), 3.52-3.50 (2H, m), 2.84-2.81 (1H, m), 2.70 (2H, t, J = 7.9 Hz), 2.11-2.09 (1H, m), 1.06 (2H, t, J = 7.6 Hz). 92 Reference Example  81

LCMS: [M + H]+/Rt = 379.09/0.453 min^(C) 93 Reference Example  60

LCMS: [M + H]+/Rt = 375.01/0.304 min^(A) ¹H-NMR (CD₃OD) δ: 7.16 (1H, d, J = 7.3 Hz), 6.35-6.33 (1H, m), 5.08-5.06 (1H, m), 4.62-4.59 (1H, m), 4.39-4.37 (1H, m), 4.22 (1H, d, J = 9.8 Hz), 3.97 (1H, d, J = 11.0 Hz), 3.52 (1H, t, J = 9.8 Hz), 3.38-3.35 (1H, m), 3.25-3.23 (1H, m), 2.93 (1H, t, J = 10.4 Hz), 2.70-2.68 (3H, m), 2.48-2.45 (1H, m), 2.39-2.35 (1H, m), 2.26-2.24 (1H, m), 1.73-1.68 (1H, m), 1.07 (2H, t, J = 7.9 Hz). 94 Reference Example 124

LCMS: [M + H]+/Rt = 466.23/0.486 min^(C) ¹H-NMR (D₂O) δ: 6.51 (1H, d, J = 8.5 Hz), 5.67 (1H, dd, J = 8.5, 2.7 Hz), 4.64-4.59 (1H, m), 4.22-4.16 (1H, m), 4.00-3.84 (3H, m), 3.65 (1H, dd, J = 10.7, 3.4 Hz), 2.87-2.82 (1H, m), 2.68 (3H, d, J = 3.1 Hz), 2.57 (3H, d, J = 8.5 Hz), 2.49-2.44 (1H, m), 2.23-2.14 (4H, m), 1.99-1.90 (2H, m), 1.07-1.03 (1H, m), 0.00 (2H, t, J = 7.0 Hz).

TABLE 3-18 95 Reference Example 125

LCMS: [M + H]⁺/Rt = 466.28/0.482 min^(C) ¹H-NMR (D₂O) δ: 6.51 (1H, d, J = 7.9 Hz), 5.67 (1H, dd, J = 7.9, 2.4 Hz), 4.64-4.59 (1H, m), 4.19 (1H, dd, J = 15.9, 9.2 Hz), 4.00-3.84 (3H, m), 3.64 (1H, dd, J = 11.0, 3.4 Hz), 2.90-2.85 (1H, m), 2.68 (3H, d, J = 3.7 Hz), 2.57 (3H, d, J = 7.9 Hz), 2.52-2.46 (1H, m), 2.23-2.17 (4H, m), 1.98-1.92 (2H, m), 1.07 (1H, dd, J = 8.9, 4.0 Hz), 0.00 (2H, t, J = 7.0 Hz). 96 Reference Example  62

LCMS: [M + H]⁺/Rt = 393.10/0.477 min^(C) ¹H-NMR (D₂O) δ: 6.49 (1H, d, J = 7.9 Hz), 5.67 (1H, d, J = 7.9 Hz), 4.98 (1H, dq, J = 53.1, 4.3 Hz), 4.64-4.58 (1H, m), 4.42-4.39 (1H, m), 4.20-4.15 (1H, m), 3.97 (1H, dd, J = 10.4, 6.1 Hz), 3.88 (1H, dd, J = 10.4, 3.7 Hz), 3.64 (1H, dd, J = 11.0, 3.1 Hz), 3.41-3.31 (1H, m), 3.07 (1H, dt, J = 20.0, 13.0 Hz), 2.84-2.67 (1H, m), 2.29-2.22 (1H, m), 2.18 (2H, t, J = 7.0 Hz), 2.15-2.02 (1H, m), 1.59-1.47 (1H, m), 0.00 (2H, t, J = 7.0 Hz).

The names of the compounds of Examples 90 to 96 are described below.

-   2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 90) -   2-hydroxy-7-({1-[(4R)-4-(trifluoromethyl)-D-prolyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid (Example 91) -   7-({1-[(4S)-4-fluoro-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 92) -   2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 93) -   8-[(1-{[(3R,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 94) -   8-[(1-{[(3S,5R)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 95) -   8-[(1-{[(2R,4S)-4-fluoropyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 96)

A reaction, work-up, and purification were performed using the compounds of Reference Examples 82 to 105 and 117 to 123 as the starting materials by the same method described in Example 38 to obtain the following Example compounds 97 to 127 (corresponding starting materials are not in order). However, if hydrochloride is the final product (Examples 119, 120, and 123), the hydrochloride was obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-19 Starting Example material Structural formula NMR and/or LCMS  97 Reference Example  82

LCMS: [M + H]⁺/Rt = 397.3/1.08 min^(B) ¹H-NMR (CD₃OD) δ: 7.63 (1H, d, J = 8.1 Hz), 5.95 (1H, d, J = 8.1 Hz), 5.03-4.95 (1H, m), 4.64-4.52 (1H, m), 4.39-4.25 (2H, m), 4.09-3.95 (2H, m), 3.37-3.01 (2H, m), 2.62-2.20 (4H, m), 0.46 (2H, t, J = 8.1 Hz).  98 Reference Example 117

LCMS: [M + H]⁺/Rt = 377.2/0.65 min^(B) ¹H-NMR (CD₃OD) δ: 6.73 (1H, d, J = 8.1 Hz), 5.94 (1H, d, J = 8.1 Hz), 5.02-4.92 (1H, m), 4.62-4.52 (1H, m), 4.42-4.22 (3H, m), 4.08-4.00 (1H, m), 3.92-3.86 (1H, m), 3.22-3.16 (1H, m), 2.80-2.75 (1H, m), 2.57 (2H, t, J = 8.1 Hz), 2.10-2.01 (1H, m), 1.89-1.76 (1H, m), 0.45 (2H, t, J = 8.1 Hz).  99 Reference Example  83

LCMS: [M + H]⁺/Rt = 389.3/0.91 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 4.99-4.89 (1H, m), 4.54-4.48 (1H, m), 4.33-4.19 (2H, m), 4.02-3.97 (1H, m), 3.00-2.95 (2H, m), 2.63-2.53 (4H, m), 2.19 (2H, d, J = 8.1 Hz), 1.99-1.81 (1H, m), 1.73-1.65 (2H, m), 1.33-1.14 (2H, m), 0.43 (2H, t, J = 8.1 Hz). 100 Reference Example  84

LCMS: [M + H]⁺/Rt = 361.2/0.93 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.58-4.52 (1H, m), 4.32-4.25 (2H, m), 4.02-3.97 (1H, m), 3.09-2.76 (5H, m), 2.56 (2H, d, J = 8.1 Hz), 2.03-1.85 (2H, m), 0.43 (2H, t, J = 8.1 Hz).

TABLE 3-20 101 Reference Example 118

LCMS: [M + H]⁺/Rt = 377.2/0.54 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.94 (1H, d, J = 8.1 Hz), 5.04-4.94 (1H, m), 4.60-4.49 (1H, m), 4.40-4.24 (3H, m), 4.10-4.01 (1H, m), 3.72-3.66 (1H, m), 3.01-2.97 (1H, m), 2.81-2.75 (1H, m), 2.56 (2H, d, J = 8.1 Hz), 2.40-2.26 (1H, m), 1.76-1.67 (1H, m), 0.44 (2H, t, J = 8.1 Hz). 102 Reference Example 120

LCMS: [M + H]⁺/Rt = 376.2/0.31 min^(B) ¹H-NMR (CD₃OD) δ: 6.73 (1H, d, J = 8.1 Hz), 5.95 (1H, d, J = 8.1 Hz), 5.02-4.94 (1H, m), 4.61-4.49 (1H, m), 4.38-4.21 (2H, m), 4.09-4.00 (1H, m), 3.75-3.61 (1H, m), 3.49-3.29 (1H, m), 3.00-2.78 (1H, m), 2.56 (2H, d, J = 8.1 Hz), 2.41-2.18 (1H, m), 1.64-1.29 (2H, m), 0.45 (2H, t, J = 8.1 Hz). 103 Reference Example 121

LCMS: [M + H]⁺/Rt = 418.3/0.74 min^(B) ¹H-NMR (CD₃OD) δ: 6.77 (1H, d, J = 8.1 Hz), 5.97 (1H, d, J = 8.1 Hz), 5.02-4.96 (1H, m), 4.62-4.52 (1H, m), 4.40-4.23 (3H, m), 4.10-4.03 (1H, m), 3.76-3.72 (1H, m), 3.02-2.86 (2H, m), 2.57 (2H, d, J = 8.1 Hz), 2.48-2.35 (1H, m), 1.92 (3H, s), 1.75-1.63 (1H, m), 0.54-0.45 (2H, m). 104 Reference Example 119

LCMS: [M + H]⁺/Rt = 377.2/0.55 min^(B) ¹H-NMR (CD₃OD) δ: 6.76 (1H, d, J = 8.1 Hz), 5.98 (1H, d, J = 8.1 Hz), 5.03-4.97 (1H, m), 4.62-4.49 (2H, m), 4.39-4.22 (2H, m), 4.11-4.05 (1H, m), 3.69-3.65 (1H, m), 3.35-3.19 (1H, m), 2.89-2.80 (1H, m), 2.57 (2H, d, J = 8.1 Hz), 2.11-1.80 (2H, m), 0.50-0.42 (2H, m). 105 Reference Example  85

LCMS: [M + H]⁺/Rt = 389.3/1.18 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.02-4.96 (1H, m), 4.59-4.47 (1H, m), 4.39-4.20 (2H, m), 4.08-4.00 (1H, m), 3.83-3.77 (1H, m), 2.80-2.54 (4H, m), 2.00-1.88 (1H, m), 1.59-1.50 (1H, m), 1.09 (3H, s), 1.06 (3H, s), 0.44 (2H, t, J = 8.1 Hz). 106 Reference Example  86

LCMS: [M + H]⁺/Rt = 375.2/0.99 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.92 (1H, d, J = 8.1 Hz), 4.98-4.91 (1H, m), 4.53-4.47 (1H, m), 4.33-4.19 (2H, m), 4.03-3.96 (1H, m), 3.37-3.33 (1H, m), 3.08-2.80 (2H, m), 2.56 (2H, t, J = 8.1 Hz), 2.35-2.30 (2H, m), 2.06-1.90 (1H, m), 1.85-1.72 (2H, m), 1.43-1.29 (1H, m), 0.42 (2H, t, J = 8.1 Hz).

TABLE 3-21 107 Reference Example 87

LCMS: [M + H]⁺/Rt = 375.3/0.96 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.63-4.52 (1H, m), 4.36-4.22 (2H, m), 4.06-3.96 (1H, m), 3.09-3.02 (1H, m), 2.66-2.53 (3H, m), 1.94-1.75 (2H, m), 1.63-1.27 (5H, m), 0.43 (2H, t, J = 8.1 Hz). 108 Reference Example 88

LCMS: [M + H]⁺/Rt = 375.3/0.99 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 4.99-4.92 (1H, m), 4.60-4.53 (1H, m), 4.31-4.25 (2H, m), 4.01-3.95 (1H, m), 2.95 (2H, t, J = 8.1 Hz), 2.66-2.39 (5H, m), 1.88-1.43 (4H, m), 0.43 (2H, t, J = 8.1 Hz). 109 Reference Example 89

LCMS: [M + H]⁺/Rt = 375.3/0.95 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 4.99-4.90 (1H, m), 4.58-4.53 (1H, m), 4.31-4.25 (2H, m), 4.01-3.96 (1H, m), 3.08-2.99 (2H, m), 2.66-2.40 (5H, m), 1.71-1.51 (4H, m), 0.43 (2H, t, J = 8.1 Hz). 110 Reference Example 90

LCMS: [M + H]⁺/Rt = 362.2/1.31 min^(B) ¹H-NMR (CD₃OD) δ: 6.63 (1H, d, J = 8.1 Hz), 5.84 (1H, d, J = 8.1 Hz), 4.91-4.83 (1H, m), 4.62-4.52 (1H, m), 4.35-4.21 (3H, m), 3.97-3.68 (3H, m), 2.47 (2H, t, J = 8.1 Hz), 2.19-2.01 (1H, m), 1.96-1.71 (3H, m), 0.41-0.31 (2H, m). 111 Reference Example 91

LCMS: [M + H]⁺/Rt = 437.0/1.34 min^(B) ¹H-NMR (CD₃OD) δ: 7.31-7.26 (4H, m), 7.21-7.15 (1H, m), 6.70 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.05-4.94 (1H, m), 4.65-4.54 (1H, m), 4.42-4.26 (2H, m), 4.11-4.03 (1H, m), 3.89 (1H, t, J = 8.1 Hz), 3.77-3.65 (1H, m), 3.39-3.20 (1H, m), 3.07-2.96 (1H, m), 2.85-2.53 (3H, m), 1.94-1.77 (1H, m), 0.42 (2H, t, J = 8.1 Hz). 112 Reference Example 92

LCMS: [M + H]⁺/Rt = 373.3/0.96 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.91 (1H, d, J = 8.1 Hz), 5.00-4.91 (1H, m), 4.54-4.46 (1H, m), 4.36-4.26 (2H, m), 4.05-3.99 (2H, m), 2.77-2.71 (1H, m), 2.58-2.39 (3H, m), 1.95-1.87 (1H, m), 1.52-1.43 (1H, m), 0.63-0.55 (1H, m), 0.48-0.38 (3H, m).

TABLE 3-22 113 Reference Example  93

LCMS: [M + H]⁺/Rt = 375.2/0.85 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.92 (1H, d, J = 8.1 Hz), 5.00-4.92 (1H, m), 4.65-4.55 (1H, m), 4.38-4.26 (2H, m), 4.07-3.99 (1H, m), 3.08-3.02 (1H, m), 2.95-2.88 (1H, m), 2.56 (2H, t, J = 8.1 Hz), 2.30-2.10 (5H, m), 1.88-1.79 (3H, m), 0.43 (2H, t, J = 8.1 Hz). 114 Reference Example  94

LCMS: [M + H]⁺/Rt = 389.3/0.95 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.97-5.93 (1H, m), 4.96-4.86 (1H, m), 4.63-4.57 (1H, m), 4.31-4.20 (2H, m), 4.02-3.96 (1H, m), 3.00-2.84 (2H, m), 2.62-2.50 (3H, m), 2.35-2.23 (1H, m), 2.09-1.96 (3H, m), 1.89-1.80 (1H, m), 1.74-1.54 (2H, m), 1.26-1.10 (1H, m), 0.43 (2H, t, J = 8.1 Hz). 115 Reference Example  95

LCMS: [M + H]+/Rt = 391.3/0.9 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.93 (1H, d, J = 8.1 Hz), 5.00-4.80 (1H, m), 4.58-4.49 (1H, m), 4.33-4.21 (2H, m), 4.02-3.98 (1H, m), 3.90-3.76 (2H, m), 3.64-3.51 (1H, m), 2.95-2.47 (6H, m), 2.37-2.29 (1H, m), 2.22-2.12 (1H, m), 0.44 (2H, t, J = 8.1 Hz). 116 Reference Example  96

LCMS: [M + H]⁺/Rt = 361.2/0.84 min^(B) ¹H-NMR (CD₃OD) δ: 6.72 (1H, d, J = 8.1 Hz), 5.94 (1H, d, J = 8.1 Hz), 5.16-5.03 (1H, m), 4.56-4.50 (2H, m), 4.37-4.26 (2H, m), 3.78-3.65 (1H, m), 3.57-3.44 (3H, m), 2.89-2.68 (2H, m), 2.61-2.53 (3H, m), 0.43 (2H, t, J = 8.1 Hz). 117 Reference Example  97

LCMS: [M + H]⁺/Rt = 390.3/0.34 min^(B) ¹H-NMR (CD₃OD) δ: 6.70 (1H, d, J = 8.1 Hz), 5.95-5.91 (1H, m), 5.10-4.97 (1H, m), 4.44-3.61 (4H, m), 3.35-1.52 (10H, m), 0.43 (2H, t, J = 8.1 Hz). 118 Reference Example  98

LCMS: [M + H]⁺/Rt = 389.3/0.98 min^(B) ¹H-NMR (CD₃OD) δ: 6.80-6.73 (1H, m), 5.98-5.91 (1H, m), 5.00-4.76 (1H, m), 4.35-3.79 (4H, m), 3.22-3.00 (3H, m), 2.65-2.51 (2H, m), 2.33-1.29 (8H, m), 0.55-0.28 (2H, m). 119 Reference Example 122

LCMS: [M + H]⁺/Rt = 376.2/0.41 min^(B) ¹H-NMR (CD₃OD) δ: 7.18 (1H, d, J = 8.1 Hz), 6.41-6.30 (1H, m), 5.22-5.10 (1H, m), 4.89-4.69 (2H, m), 4.57-4.26 (2H, m), 4.20-4.05 (2H, m), 3.93-3.86 (1H, m), 3.57-3.47 (1H, m), 2.70 (2H, t, J = 8.1 Hz), 2.64-2.45 (2H, m), 1.07 (2H, t, J = 8.1 Hz).

TABLE 3-23 120 Reference Example 123

LCMS: [M + H]⁺/Rt = 418.2/0.89 min^(B) ¹H-NMR (CD₃OD) δ: 7.18 (1H, d, J = 8.1 Hz), 6.41-6.30 (1H, m), 5.20-5.12 (1H, m), 4.77-4.26 (5H, m), 4.14-4.05 (1H, m), 3.67-3.60 (1H, m), 3.36-3.30 (1H, m), 2.71 (2H, t, J = 8.1 Hz), 2.48-2.21 (2H, m), 1.98 (3H, s), 1.07 (2H, t, J = 8.1 Hz). 121 Reference Example  99

LCMS: [M + H]⁺/Rt = 404.3/0.34 min^(B) ¹H-NMR (CD₃OD) δ: 6.74-6.69 (1H, m), 5.98-5.92 (1H, m), 5.03-4.94 (1H, m), 4.64-4.47 (1H, m), 4.39-4.19 (2H, m), 4.05-3.97 (1H, m), 3.19-2.46 (7H, m), 2.00-1.80 (1H, m), 1.71-1.28 (4H, m), 0.43 (2H, t, J = 8.1 Hz). 122 Reference Example 104

LCMS: [M + H]⁺/Rt = 389.3/1.05 min^(B) ¹H-NMR (CD₃OD) δ: 6.74-6.69 (1H, m), 5.91-5.86 (1H, m), 4.94-4.83 (1H, m), 4.48-3.97 (4H, m), 3.12-2.86 (2H, m), 2.71-2.54 (3H, m), 2.26-2.14 (2H, m), 1.85-1.12 (6H, m), 0.42 (2H, t, J = 8.1 Hz). 123 Reference Example 105

LCMS: [M + H]⁺/Rt = 404.1/0.84 min^(B) ¹H-NMR (CD₃OD) δ: 7.18 (1H, d, J = 8.2 Hz), 6.41-6.31 (1H, m), 5.20-5.10 (1H, m), 4.81-4.64 (1H, m), 4.58-4.42 (2H, m), 4.38-4.25 (1H, m), 4.18-4.05 (1H, m), 3.68-3.50 (2H, m), 3.38-3.26 (1H, m), 2.85-2.67 (3H, m), 2.16-2.06 (1H, m), 1.06 (2H, t, J = 8.1 Hz). 124 Reference Example 100

LCMS: [M + H]+/Rt = 375.2/0.89 min^(B) 1¹H-NMR (CD₃OD) δ: 6.77-6.62 (1H, m), 6.00-5.85 (1H, m), 4.99-4.91 (1H, m), 4.57-4.44 (1H, m), 4.35-4.16 (2H, m), 4.04-3.92 (1H, m), 3.10-2.81 (3H, m), 2.62-2.40 (4H, m), 2.29-2.19 (2H, m), 2.10-1.96 (1H, m), 1.56-1.37 (1H, m), 0.48-0.36 (2H, m). 125 Reference Example 101

LCMS: [M + H]+/Rt = 375.1/0.92 min^(B) ¹H-NMR (CD₃OD) δ: 6.75-6.64 (1H, m), 5.99-5.88 (1H, m), 5.01-4.89 (1H, m), 4.59-4.42 (1H, m), 4.37-4.15 (2H, m), 4.03-3.90 (1H, m), 3.12-2.84 (3H, m), 2.61-2.39 (4H, m), 2.31-2.17 (2H, m), 2.11-1.95 (1H, m), 1.59-1.40 (1H, m), 0.47-0.32 (2H, m). 126 Reference Example 102

LCMS: [M + H]+/Rt = 375.1/0.99 min^(B) ¹H-NMR (CD₃OD) δ: 6.77-6.65 (1H, m), 5.96-5.86 (1H, m), 4.97-4.84 (1H, m), 4.56-3.94 (4H, m), 3.41-3.26 (1H, m), 3.09-2.75 (2H, m), 2.62-2.49 (2H, m), 2.37-2.23 (2H, m), 2.09-1.70 (3H, m), 1.47-1.25 (1H, m), 0.49-0.33 (2H, m).

TABLE 3-24 127 Reference Example 103

LCMS: [M + H]+/Rt = 375.0/0.93 min^(B) ¹H-NMR (CD₃OD) δ: 6.69 (1H, d, J = 8.2 Hz), 5.91 (1H, d, J = 8.2 Hz), 4.98- 4.85 (1H, m), 4.56-4.46 (1H, m), 4.35- 4.17 (2H, m), 4.05-3.94 (1H, m), 3.38- 3.26 (1H, m), 3.03-2.73 (2H, m), 2.61- 2.49 (2H, m), 2.37-2.26 (2H, m), 2.03- 1.88 (1H, m), 1.85-1.67 (2H, m), 1.46- 1.24 (1H, m), 0.46-0.37 (2H, m).

The names of the compounds of Examples 97 to 127 are described below.

-   8-{[1-(4,4-difluoro-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 97) -   4,4-dihydroxy-8-({1-[(4R)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 98) -   4,4-dihydroxy-8-({1-[(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 99) -   4,4-dihydroxy-8-{[1-(pyrrolidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 100) -   4,4-dihydroxy-8-({1-[(4S)-4-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 101) -   8-({1-[(4S)-4-amino-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 102) -   8-({1-[(4S)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 103) -   4,4-dihydroxy-8-({1-[(3R)-3-hydroxy-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),     7,9-triene-7-carboxylic acid disodium salt (Example 104) -   8-{[1-(4,4-dimethyl-L-prolyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 105) -   4,4-dihydroxy-8-({1-[(pyrrolidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 106) -   4,4-dihydroxy-8-{[1-(piperidine-2-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 107) -   4,4-dihydroxy-8-{[1-(piperidine-3-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 108) -   4,4-dihydroxy-8-{[1-(piperidine-4-carbonyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 109) -   4,4-dihydroxy-8-({1-[(2S)-oxolane-2-carbonyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 110) -   4,4-dihydroxy-8-({1-[(4R)-4-phenyl-L-prolyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 111) -   8-({1-[(1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carbonyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 112) -   4,4-dihydroxy-8-{[1-(1-methyl-L-prolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 113) -   4,4-dihydroxy-8-({1-[(piperidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 114) -   4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 115) -   8-({1-[(azetidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 116) -   8-({1-[amino(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 117) -   4,4-dihydroxy-8-({1-[3-(pyrrolidin-2-yl)propanoyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 118) -   7-({1-[(4R)-4-amino-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid dihydrochloride (Example 119) -   7-({1-[(4R)-4-acetamido-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 120) -   8-({1-[amino(piperidin-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 121) -   4,4-dihydroxy-8-({1-[(piperidin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 122) -   7-({1-[(4S)-4-carbamoyl-L-prolyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 123) -   4,4-dihydroxy-8-[(1-{[(3R)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 124) -   4,4-dihydroxy-8-[(1-{[(3S)-pyrrolidin-3-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 125) -   4,4-dihydroxy-8-[(1-{[(2R)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 126) -   4,4-dihydroxy-8-[(1-{[(2S)-pyrrolidin-2-yl]acetyl}azetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 127)

The following Example compounds 128 and 129 were obtained by performing a reaction, work-up, and purification using the compounds of Reference Examples 61 and 126, respectively, as the starting materials by the same method described in Example 36, further dissolving the resulting crude product in water, adding an aqueous 2 N sodium hydroxide solution, and purifying by reversed phase chromatography.

TABLE 3-25 Exam- Starting ple material Structural formula NMR and/or LCMS 128 Reference Example 61

LCMS: [M + H]⁺/Rt = 389.96/0.446 min^(F) ¹H-NMR (D₂O) δ: 6.90 (1H, d, J = 8.2 Hz), 6.07 (1H, d, J = 8.2 Hz), 5.01 (1H, m), 4.60 (1H, m), 4.28-4.40 (2H, m), 4.05 (1H, m), 2.94-3.09 (4H, m), 2.58-2.81 (4H, m), 2.45 (1H, m), 2.22-2.31 (2H, m), 0.38 (2H, m). 129 Reference Example 126

LCMS: [M + H]⁺/Rt = 438.95/0.555 min^(F) ¹H-NMR (D₂O) δ: 6.90 (1H, d, J = 8.2 Hz), 6.07 (1H, d, J = 8.2 Hz), 5.03 (1H, m), 4.65 (1H, m), 4.42-4.32 (2H, m), 4.08 (1H, m), 3.60 (1H, m), 3.47- 3.12 (5H, m), 2.96-2.79 (2H, m), 2.60 (2H, m), 2.40 (1H, m), 0.39 (2H, m).

The names of the compounds of Examples 128 and 129 are described below.

-   4,4-dihydroxy-8-({1-[(piperazin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 128) -   8-({1-[(1,1-dioxo-1λ⁶-thiomorpholin-2-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic     acid disodium salt (Example 129)

The following Example compounds 130 to 137 were obtained by performing a reaction, work-up, and purification using the compounds of Reference Examples 128 and 131 to 137 as the starting materials (corresponding starting materials are not in order) by the same method described in Example 38, purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-26 Exam- Starting ple material Structural formula NMR and/or LCMS 130 Reference Example 131

LCMS: [M + H]⁺/Rt=406.1/0.86 min^(B) ¹H-NMR (CD₃OD) δ: 7.19-7.11 (1H, m), 6.36-6.14 (1H, m), 5.16- 4.99 (1H, m), 4.74-4.65 (1H, m), 4.54-4.27 (2H, m), 4.12-3.96 (2H, m), 3.42-3.20 (2H, m), 2.73-2.54 (2H, m), 2.11-1.89 (5H, m), 1.09-0.68 (2H, m). 131 Reference Example 132

LCMS: [M + H]⁺/Rt = 378.1/0.54 min^(B) ¹H-NMR (CD₃OD) δ: 7.19-7.11 (1H, m), 6.34-6.10 (1H, m), 5.13- 4.99 (1H, m), 4.66-4.52 (1H, m), 4.47-4.01 (4H, m), 2.94-2.50 (4H, m), 1.09-0.64 (2H, m). 132 Reference Example 133

LCMS: [M + H]⁺/Rt = 406.1/0.94 min^(B) ¹H-NMR (CD₃OD) δ: 7.18-7.10 (1H, m], 6.64-6.09 (1H, m), 5.14- 5.03 (1H, m), 4.80-4.66 (1H, m), 4.46-4.27 (3H, m), 4.04-3.87 (2H, m), 2.80-2.52 (2H, m), 1.51-1.46 (3H, m), 1.36-1.33 (3H, m), 1.09-0.65 (2H, m). 133 Reference Example 135

LCMS: [M + H]⁺/Rt = 392.1/ 0.88 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.1 Hz), 6.39-6.28 (1H, m), 5.17-5.06 (1H, m), 4.99-4.80 (1H, m), 4.73-3.94 (4H, m), 3.74-3.67 (2H, m), 2.70 (2H, t, J = 8.1 Hz), 1.34 (3H, d, J = 8.1 Hz), 1.06 (2H, t, J = 8.1 Hz). 134 Reference Example 136

LCMS: [M + H]⁺/Rt = 450.1/ 0.92 min^(B) ¹H-NMR (CD₃OD) δ: 8.67-8.56 (1H, m), 7.18-7.10 (1H, m), 6.34- 6.10 (1H, m), 5.13-5.05 (1H, m), 4.93-4.66 (1H, m), 4.52-4.27 (3H, m), 4.23-4.13 (1H, m), 4.04-3.95 (1H, m), 3.08-2.52 (4H, m), 1.36-1.33 (3H, m), 1.09- 0.66 (2H, m). 135 Reference Example 134

LCMS: [M + H]⁺/Rt = 449.1/ 0.85 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.1 Hz), 6.38-6.28 (1H, m), 5.15-5.05 (1H, m), 4.92-4.64 (1H, m), 4.47-4.27 (3H, m), 4.22-4.15 (1H, m), 4.03-3.95 (1H, m), 2.96-2.86 (1H, m), 2.76- 2.65 (3H, m), 1.34 (3H, d, J = 5.4 Hz), 1.07 (2H, t, J = 8.1 Hz).

TABLE 3-27 136 Reference Example 128

LCMS: [M + H]⁺/Rt = 422.1/0.88 min^(B) ¹H-NMR (CD₃OD) δ: 8.84-8.56 (1H, m), 7.18-7.10 (1H, m), 6.34- 6.09 (1H, m), 5.13-4.59 (2H, m), 4.51-4.26 (3H, m), 4.13- 3.77 (4H, m), 2.79-2.51 (2H, m), 1.37-1.33 (3H, m), 1.09-0.64 (2H, m). 137 Reference Example 137

LCMS: [M + H]⁺/Rt = 379.0/0.71 min^(B) ¹H-NMR (CD₃OD) δ: 7.17 (1H, d, J = 8.2 Hz), 6.78-6.32 (1H, m), 5.14-5.04 (1H, m), 4.67-4.61 (1H, m), 4.47-4.38 (1H, m), 4.31-4.22 (2H, m), 4.05-3.61 (1H, m), 3.00-2.78 (2H, m), 2.70 (2H, t, J = 8.1 Hz), 1.06 (2H, t, J = 8.1 Hz).

The names of the compounds of Examples 130 to 137 are described below.

-   7-({1-[(2S)-4-acetamido-2-aminobutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 130) -   7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 131) -   7-{[1-(L-alanyl-L-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 132) -   7-{[1-(glycyl-D-alanyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 133) -   N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-α-asparagine     hydrochloride (Example 134) -   N¹-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-aspartamide     hydrochloride (Example 135) -   N-[(2R)-1-{3-[(8-carboxy-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-7-yl)oxy]azetidin-1-yl}-1-oxopropan-2-yl]-D-serinamide     hydrochloride (Example 136) -   7-({1-[(3S)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 137)

The compounds of Reference Examples 138 and 139 were used as the starting materials to perform a reaction and work-up by the same method described in Example 4. Each of Example compounds 138 and 139 were obtained from purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-28 Exam- Starting ple material Structural formula NMR and/or LCMS 138 Reference Example 138

LCMS: [M + H]⁺/Rt = 401.26/ 0.58 min^(I) ¹H-NMR (500 MHz, CD₃OD) δ: 9.10-9.07 (1H, m), 7.93 (brs, 1H), 7.15 (1H, d, J = 8.0 Hz), 6.37- 6.22 (1H, m), 5.61-5.54 (1H, m), 5.16-4.75 (2H, m), 4.61-3.76 (3H, m), 2.74-2.69 (5H, m), 1.06 (2H, t, J = 8.0 Hz). 139 Reference Example 139

LCMS: [M + H]⁺/Rt = 415.25/ 1.03 min^(I) ¹H-NMR (500 MHz, CD₃OD) δ: 8.91 (1H, brs), 7.95 (1H, brs), 7.14 (1H, d, J = 8.0 Hz), 6.38- 6.23 (1H, m), 5.75-5.58 (1H, m), 5.16-3.94 (6H, m), 3.01-3.81 (5H, m), 2.75-2.65 (5H, m), 1.06 (2H, t, J = 8.0 Hz).

The names of the compounds of Examples 138 and 139 are described below.

-   2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid dihydrochloride (Example 138) -   2-hydroxy-7-({1-[(1H-imidazol-4-yl)(methylamino)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid dihydrochloride

Example 139 Example 140: 2-hydroxy-7-{[1-(2-methyl-D-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic Acid

A reaction, work-up, and purification were performed using the compound of Reference Example 140 (245 mg, 0.317 mmol) as the starting material by the same method described in Example 36 to obtain the title compound (21.8 mg) as a white solid.

¹H-NMR (0.1M HCl in CD₃OD) δ: 7.18 (1H, d, J=8.5 Hz), 6.35 (1H, d, J=8.5 Hz), 5.14-5.10 (2H, m), 4.50-4.43 (2H, m), 4.12-4.04 (1H, m), 3.91 (1H, d, J=12.2 Hz), 3.72 (1H, d, J=12.2 Hz), 2.70 (2H, t, J=7.6 Hz), 1.52 (3H, s), 1.05 (2H, t, J=7.6 Hz).

LCMS: [M+H]⁺/Rt=365.09/0.447 min^(C)

The following Example compounds 141 to 148 were obtained by performing a reaction using the compounds of Reference Examples 141, 143, and 150 to 155, respectively, as the starting materials by the same method described in Example 36, followed by, as a work-up, concentrating a reaction mixture under reduced pressure and then purifying the mixture by reversed phase chromatography (Column: YMC-Actus pro C18, solution A: 0.05% TFA/water, solution B: 0.03% TFA/acetonitrile). However, if hydrochloride is the final product (Example 145), the hydrochloride was obtained from purifying the compound by reversed phase chromatography, followed by addition of hydrochloric acid and concentration.

TABLE 3-29 Exam- Starting ple material Structural formula NMR and/or LCMS 141 Reference Example 141

LCMS: [M + H]⁺/Rt = 365/1.414 min^(G) ¹H-NMR (D₂O) δ: 7.08-6.89 (1H, m), 6.14-5.94 (1H, m), 4.96-4.67 (2H, m), 4.36-4.29 (2H, m), 4.02-3.92 (1H, m), 3.81-3.73 (1H, m), 3.63- 3.56 (1H, m), 2.52-2.25 (2H, m), 1.38- 1.33 (3H, m), 0.92-0.43 (2H, m). 142 Reference Example 143

LCMS: [M + H]⁺/Rt = 404/1.400 min^(G) ¹H-NMR (D₂O) δ: 7.11-6.91 (1H, m), 6.15-5.89 (1H, m), 4.95-4.81 (1H, m), 4.48-4.38 (1H, m), 4.32-3.84 (4H, m), 3.57-3.39 (3H, m), 3.36-3.29 (1H, m), 2.99-2.67 (2H, m), 2.53-2.36 (2H, m), 0.94-0.45 (2H, m). 143 Reference Example 150

LCMS: [M + H]⁺/Rt = 407/1.175 min^(G) ¹H-NMR (D₂O) δ: 7.09-6.89 (1H, m), 6.15-5.91 (1H, m), 4.94-4.63 (2H, m), 4.50-3.84 (4H, m), 2.53-2.33 (6H, m), 1.92-1.74 (2H, m), 0.93-0.43 (2H, m). 144 Reference Example 151

LCMS: [M + H]⁺/Rt = 379/1.400 min^(G) ¹H-NMR (D₂O) δ: 6.94-6.80 (1H, m), 5.98-5.78 (1H, m), 4.35-3.36 (6H, m), 2.67 (2H, s), 2.35-2.20 (2H, m), 0.91- 0.60 (2H, m).

TABLE 3-30 145 Reference Example 152

LCMS: [M + H]⁺/Rt = 393/1.217 min^(G) ¹H-NMR (D₂O) δ: 7.05-6.84 (1H, m), 6.13-5.85 (1H, m), 4.91-4.71 (1H, m), 4.47-3.87 (5H, m), 2.52-2.21 (4H, m), 2.01 (2H, brs), 0.91-0.40 (2H, m). 146 Reference Example 153

LCMS: [M + H]⁺/Rt = 406/1.223 min^(G) ¹H-NMR (D₂O) δ: 7.05-6.82 (1H, m), 6.14-5.87 (1H, m), 4.92-4.74 (1H, m), 4.28-4.03 (4H, m), 3.46 (1H, brs), 2.50-1.74 (8H, m), 0.92-0.39 (2H, m). 147 Reference Example 154

LCMS: [M + H]⁺/Rt = 378/1.208 min^(G) ¹H-NMR (D₂O) δ: 7.02-6.82 (1H, m), 6.08-5.83 (1H, m), 4.88-4.71 (1H, m), 4.39-3.83 (5H, m), 2.68 (2H, brs), 2.52-2.16 (2H, m), 0.70-0.37 (2H, m). 148 Reference Example 155

LCMS: [M + H]⁺/Rt = 392/1.171 min^(G) ¹H-NMR (D₂O) δ: 7.07-6.81 (1H, m), 6.10-5.84 (1H, m), 4.78-4.67 (1H, m), 4.42-3.80 (5H, m), 2.50-2.33 (2H, m), 2.17 (2H, brs), 1.98-1.96 (2H, m), 0.91-0.38 (2H, m).

The names of the compounds of Examples 141 to 148 are described below.

-   2-hydroxy-7-{[1-(2-methyl-L-seryl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 141) -   2-hydroxy-7-({1-[(3-oxopiperazin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 142) -   7-({1-[(3S)-3-amino-5-carboxypentanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 143) -   7-({1-[(3R)-3-amino-3-carboxypropanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 144) -   7-({1-[(4R)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 145) -   7-({1-[(3S)-3,6-diamino-6-oxohexanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 146) -   7-{[1-(D-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 147) -   7-{[1-(D-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid trifluoroacetate (Example 148)

The following Example compounds 149 and 150 were obtained by performing a reaction and work-up using the compounds of Reference Examples 146 and 147, respectively, as the starting materials by the same method described in Example 38, and purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-31 Exam- Starting ple material Structural formula NMR and/or LCMS 149 Reference Example 146

LCMS: [M + H]+/Rt = 393.1/ 0.86 min^(B) 1H-NMR (CD3OD) δ: 7.22-7.08 (1H, m), 6.38-6.06 (1H, m), 5.13-5.01 (1H, m), 4.67-4.52 (1H, m), 4.47-4.32 (1H, m), 4.28-4.18 (1H, m), 4.11-3.92 (2H, m), 2.76-2.62 (2H, m), 2.53-2.38 (2H, m), 2.28-2.04 (2H, m), 1.13-0.61 (2H, m). 150 Reference Example 147

LCMS: [M + H]⁺/Rt = 392.1/ 0.86 min^(B) 1H-NMR (CD3OD) δ: 7.24-7.08 (1H, m), 6.41-6.07 (1H, m), 5.14-5.00 (1H, m), 4.67-4.51 (1H, m), 4.46-4.32 (1H, m), 4.29-4.16 (1H, m), 4.08-3.88 (2H, m), 2.81-2.50 (2H, m), 2.49-2.34 (2H, m), 2.21-2.02 (2H, m), 1.14-0.64 (2H, m).

The names of the compounds of Examples 149 and 150 are described below.

-   7-({1-[(4S)-4-amino-4-carboxybutanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 149) -   7-{[1-(L-α-glutaminyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 150)

The following Example compounds 151 and 152 were obtained by performing a reaction and work-up using the compounds of Reference Examples 148 and 149, respectively, as the starting materials by the same method described in Example 4 and purifying the compound by reversed phase chromatography without sodium hydroxide treatment, followed by addition of hydrochloric acid and concentration.

TABLE 3-32 Exam- Starting ple material Structural formula NMR and/or LCMS 151 Reference Example 148

LCMS: [M + H]⁺/Rt = 365.24/ 1.27 min^(I). ¹H-NMR (500 MHz, CDCl₃) δ: 7.18-7.09 (1H, s), 6.32 (1H, brs), 5.13-5.07 (1H, m), 4.78-4.69 (1H, m), 4.50-4.29 (2H, m), 4.10-3.96 (2H, m), 3.81-3.78 (1H, m), 2.67 (2H, t, J = 7.4 Hz), 1.26 (3H, t, J = 5.7 Hz), 1.03 (2H, t, J = 8.1 Hz). 152 Reference Example 149

LCMS: [M + H]⁺/Rt = 365.24/ 1.23 min^(I). ¹H-NMR (500 MHz, CDCl₃) δ: 7.17-7.10 (1H, s), 6.33 (1H, brs), 5.12-5.07 (1H, m), 4.76-4.70 (1H, m), 4.51-4.30 (2H, m), 4.09-3.78 (3H, m), 2.67 (2H, brs), 1.26 (3H, t, J = 6.3 Hz), 1.03 (2H, t, J = 8.0 Hz).

The names of the compounds of Examples 151 and 152 are described below.

-   2-hydroxy-7-[(1-D-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 151) -   2-hydroxy-7-[(1-L-threonylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic     acid hydrochloride (Example 152)

Pharmacological testing methods and results thereof for representative compounds of the invention are shown hereinafter, but the present invention is not limited to the Test Examples.

Test Example 1: Evaluation of Minimum Inhibitory Concentration (MIC) of MEPM Against β-Lactamase Producing Bacteria

To evaluate the β-lactamase inhibitory activity of test compounds, the effect of combination of a test compound and a β-lactam agent against β-lactamase producing bacteria was evaluated. Meropenem (MEPM) was used as a β-lactam antimicrobial agent. The minimum inhibitory concentration (MIC) of MEPM against β-lactamase producing bacteria when a test compound was added at a fixed concentration (4 μg/mL) was measured by broth microdilution method (common ratio: 2). MIC of MEPM decreasing to less than 1/32 in combination with a test compound is indicated by A, decreasing from 1/32 to 1/16 is indicated by B, decreasing from ⅛ to ¼ is indicated by C, and decreasing to ½ or others are indicated by D. “-” represents untested cases.

TABLE 4 E. coli K. pneumoniae K. pneumoniae Example ATCC BAA-2340 ATCC BAA-2344 ATCC BAA-2524 number (KPC) (KPC) (OXA-48) 1 A A B 2 A A B 3 A A B 4 A A A 5 A B C 6 A A B 7 A A B 8 A A B 9 A A A 10 A A B 11 A B B 12 A A B 13 A A B 14 A A B 15 A A B 16 A — B 17 A B B 18 A A B 19 A A B 20 A B B 21 A B C 22 A A B 23 — A B 24 A A B 25 A A B 26 A A A 27 — A B 28 A A B 29 — A B 30 — A B 31 — A B 32 — A B 33 — A B 34 — A B 35 A A B

Test Example 2: Evaluation of Minimum Inhibitory Concentration (MIC) of MEPM Against β-Lactamase Producing Bacteria

In the same manner as Test Example 1, E. coli ATCC BAA-2469 (NDM-1), K. pneumomiae ATCC BAA-2470 (NDM-1), K. pneumomiae NCTC 13439 (VIM-1), K. pneumomiae NCTC 13440 (VIM-1), E. coli NCTC 13476 (IMP), and the like can be used to evaluate metallo-β-lactamase inhibitory activity of test compounds.

Test Example 3: Evaluation of Minimum Inhibitory Concentration (MIC) of MEPM Against β-Lactamase Producing Bacteria

To evaluate the β-lactamase inhibitory activity of test compounds, the effect of combination of a test compound and a β-lactam agent against β-lactamase producing bacteria was evaluated. Meropenem (MEPM) was used as a β-lactam antimicrobial agent. The minimum inhibitory concentration (MIC) of MEPM against β-lactamase producing bacteria when a test compound was added at a fixed concentration (4 μg/mL) was measured by broth microdilution method (common ratio: 2).

The numerical value of (MIC of MEPM in combination with a test compound)/(MIC of MEPM alone) are shown below (“−” represents untested cases).

TABLE 5-1 E. coli K. pneurnoniae K. pneumoniae ATCC ATCC ATCC Example BAA-2340 BAA-2344 BAA-2524 number (KPC) (KPC) (OXA-48) 1 0.031/8 0.063/32 0.063/1 2 0.031/8 0.031/32 0.063/1 3 0.031/8 0.063/32 0.063/1 4 0.016/4 0.031/32 0.031/2 5 0.125/8 2/32 0.125/1 6 0.031/4 0.125/32 0.063/1 7 0.031/4 0.031/32 0.063/1 8 0.031/8 0.063/32 0.063/2 9 0.016/4 0.063/32 0.031/2 10 0.031/4 0.063/32 0.063/2 11 0.063/4 2/32 0.063/1 12 0.031/4 0.063/32 0.063/1 13 0.031/8 0.063/32 0.063/2 14 0.031/8 0.125/32 0.063/2 15 0.031/8 0.063/32 0.063/1 16 0.031/8 0.125/32 0.063/1 17 0.031/8 2/32 0.063/1 18 0.016/8 0.031/32 0.063/2 19 0.016/8 0.031/32 0.063/2 20 0.031/8 2/32 0.063/1 21 0.125/8 2/32 0.125/1 22 0.016/8 0.031/32 0.063/2 23 — 0.063/32 0.063/2 24 0.016/8 0.5/32 0.063/2 25 0.016/8 0.063/32 0.063/2 26 0.016/8 0.063/32 0.031/2 27 — 0.063/32 0.063/2 28 0.016/8 0.031/32 0.063/2 29 — 0.063/32 0.063/2 30 — 0.125/32 0.125/2 31 — 0.063/32 0.063/2 32 — 0.063/32 0.063/2 33 — 0.063/32 0.063/1 34 — 0.063/32 0.063/2 35 0.031/4 0.063/32 0.063/1 36 — 0.063/16 0.063/1 37 — 0.031/16 0.031/1 38 — 0.063/16 0.063/2 39 — 1/16 0.063/2 40 — 0.063/16 0.063/1 41 — 0.063/16 0.063/1 42 — 0.063/16 0.063/2 43 — 0.063/16 0.063/1

TABLE 5-2 44 — ≤0.063/16 ≤0.063/1 45 — ≤0.063716 ≤0.063/2 46 — ≤0.063/16 ≤0.063/2 47 — ≤0.063/16 ≤0.063/2 48 — ≤0.063/16 ≤0.063/2 49 — ≤0.053/16 ≤0.063/2 50 — ≤0.063/16 ≤0.063/1 51 — ≤0.063/32 ≤0.063/2 52 — ≤0.063/16 ≤0.063/1 53 — 0.25/16 ≤0.063/1 54 — 0.25/16 ≤0.063/2 55 — ≤0.031/32 ≤0.031/1 56 — 0.125/32 ≤0.031/1 57 — ≤0.063/16 ≤0.063/1 58 — ≤0.063/16 ≤0.063/2 59 — ≤0.063/32 ≤0.063/2 60 — 0.125/32 ≤0.063/2 61 — ≤0.063/16 ≤0.063/2 62 — 0.063/16 ≤0.063/2 63 — ≤0.063/16 ≤0.063/2 64 — ≤0.063/16 ≤0.063/2 65 — ≤0.063/16 ≤0.063/2 66 — ≤0.063/16 ≤0.063/2 67 — ≤0.063/16 ≤0.063/2 68 — ≤0.063/16 ≤0.063/1 69 — ≤0.063/16 ≤0.063/1 70 — ≤0.063/16 ≤0.063/2 71 — ≤0.063/16 ≤0.063/1 72 — ≤0.063/16 ≤0.063/1 73 — ≤0.063/16 ≤0.063/2 74 — 0.25/32 0.125/1 75 — 1/32 ≤0.063/1 76 — 4/32 0.25/1 77 — ≤0.063/16 ≤0.063/2 78 — ≤0.063/16 ≤0.063/1 79 — ≤0.063/16 ≤0.063/1 80 — ≤0.063/16 ≤0.063/1 81 — ≤0.063/16 ≤0.063/1 82 — ≤0.063/16 ≤0.063/1 83 — ≤0.063/32 ≤0.063/2 84 — ≤0.063/32 ≤0.063/2 85 — ≤0.063/32 ≤0.063/2 86 — ≤0.063/32 ≤0.063/2 87 — ≤0.063/16 ≤0.063/1 88 — ≤0.063/32 ≤0.063/2 89 — ≤0.063/16 ≤0.063/1 90 — ≤0.063/16 ≤0.063/1 91 — ≤0.063/16 ≤0.063/1

TABLE 5-3 92 — ≤0.063/16 ≤0.063/2 93 — ≤0.063/16 ≤0.063/2 94 — ≤0.063/16 ≤0.063/1 95 — ≤0.063/16 ≤0.063/1 96 — ≤0.063/16 ≤0.063/1 97 — ≤0.063/16 ≤0.063/2 98 — ≤0.063/16 ≤0.063/2 99 — ≤0.063/16 ≤0.063/2 100 — ≤0.063/16 ≤0.063/2 101 — ≤0.063/16 ≤0.063/2 102 — ≤0.063/16 ≤0.063/2 103 — ≤0.063/16 ≤0.063/2 104 — ≤0.063/32 ≤0.063/2 105 — ≤0.063/32 ≤0.063/2 106 — ≤0.063/16 ≤0.063/2 107 — ≤0.063/16 ≤0.063/2 108 — ≤0.063/16 ≤0.063/2 109 — ≤0.063/16 ≤0.063/2 110 — ≤0.063/16 ≤0.063/2 111 — ≤0.063/16 ≤0.063/2 112 — ≤0.063/16 ≤0.063/2 113 — ≤0.063/16 ≤0.063/2 114 — ≤0.063/16 ≤0.063/2 115 — ≤0.063/16 ≤0.063/2 118 — ≤0.063/16 ≤0.063/2 117 — ≤0.063/16 ≤0.063/2 113 — ≤0.063/16 ≤0.063/2 119 — 0.125/16 ≤0.063/1 120 — ≤0.063/16 ≤0.063/1 121 — ≤0.063/16 ≤0.063/2 122 — ≤0.063/16 ≤0.063/2 123 — ≤0.063/32 ≤0.063/2 124 — ≤0.063/16 ≤0.063/2 125 — ≤0.063/16 ≤0.063/2 128 — ≤0.063/16 ≤0.063/2 127 — ≤0.063/16 ≤0.063/2 128 — ≤0.063/16 ≤0.063/1 129 — ≤0.063/16 ≤0.063/1 130 — ≤0.063/16 ≤0.063/1 131 — ≤0.063/16 ≤0.063/1 132 — ≤0.063/16 ≤0.063/1 133 — ≤0.063/16 ≤0.063/1 134 — ≤0.063/16 ≤0.063/1 135 — ≤0.063/16 ≤0.063/1 138 — ≤0.063/16 ≤0.063/1 137 — ≤0.063/32 ≤0.063/2 138 — ≤0.063/16 ≤0.063/2 139 — ≤0.063/16 ≤0.063/2

TABLE 5-4 140 — ≤0.063/64 ≤0.063/2 141 — ≤0.063/64 ≤0.063/2 142 — ≤0.063/64 ≤0.063/2 143 — ≤0.063/64 ≤0.063/2 144 — ≤0.063/64 ≤0.063/2 145 — ≤0.063/64 ≤0.063/2 146 — ≤0.063/64 ≤0.063/2 147 — ≤0.063/64 ≤0.063/2 148 — ≤0.063/64 ≤0.063/2 149 — 0.125/64 ≤0.063/2 150 — ≤0.063/64 ≤0.063/2 151 — ≤0.063/64 ≤0.063/2 152 — ≤0.063/64 ≤0.063/2

As disclosed above, the present invention is exemplified by the use of its preferred embodiments. However, it is understood that the scope of the present invention should be interpreted based solely on the Claims. It is also understood that any patent, any patent application, and any other references cited herein should be incorporated herein by reference in the same manner as the contents are specifically described herein.

INDUSTRIAL APPLICABILITY

The compound of the invention exhibits a potent inhibitory action against β-lactamase and is useful as a therapeutic agent and/or prophylactic agent for sepsis, febrile neutropenia, bacterial meningitis, bacterial endocarditis, otitis media, sinusitis, pneumonia, lung abscess, empyema, secondary infection of a chronic respiratory disease, pharyngolaryngitis, tonsillitis, osteomyelitis, arthritis, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, deep skin infection, lymphangitis/lymphadenitis, secondary infection of trauma, burn injury, surgical wound, or the like, urinary tract infection, genital infection, eye infection, or odontogenic infection. 

The invention claimed is:
 1. A pharmaceutical composition comprising at least one compound selected from the group of compounds consisting of: a) 7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

b) 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

c) 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

d) 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

e) 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

f) 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

g) 7-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

h) 8-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

i) 7-({1-[2-amino-2-(1H-imidazol-4-yl)(²H)ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

j) 8-({1-[2-amino-2-(1H-imidazol-4-yl)(²H)ethanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

k) 7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

l) 8-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

m) 7-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

n) 8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

o) 2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

p) 4,4-dihydroxy-8-({1-[(H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

q) 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

r) 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

s) 2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

t) 4,4-dihydroxy-8-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

u) 2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

v) 4,4-dihydroxy-8-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

w) 2-hydroxy-7-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

x) 4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

y) 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

z) 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

aa) 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

and ab) 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 2. A method for treating a bacterial infection in a patient in need thereof, comprising administering a therapeutically effective amount of at least one compound selected from the group of compounds consisting of: a) 7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

b) 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

c) 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

d) 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

e) 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

f) 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

g) 7-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

h) 8-({1-[amino(1-methyl-H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

i) 7-({1-[2-amino-2-(1H-imidazol-4-yl)(2H)ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

j) 8-({1-[2-amino-2-(1H-imidazol-4-yl)(²H)ethanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

k) 7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

1) 8-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

m) 7-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

n) 8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

o) 2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

p) 4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

q) 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

r) 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

s) 2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

t) 4,4-dihydroxy-8-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

u) 2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

v) 4,4-dihydroxy-8-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

w) 2-hydroxy-7-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

x) 4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

y) 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

z) 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

aa) 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

ab) 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or pharmaceutically acceptable salt thereof.
 3. The method claim 2, wherein the bacterial infection is sepsis, pneumonia, peritonitis, intraperitoneal abscess, cholecystitis, cholangitis, liver abscess, or a urinary tract infection.
 4. The method of claim 2, wherein an additional agent is administered to the patient concomitantly with the compound or the pharmaceutically acceptable salt thereof.
 5. The method of claim 4, wherein the additional agent is a β-lactam agent.
 6. The method of claim 4, wherein the additional agent is selected from the group consisting of cefepime, ceftazidime, biapenem, doripenem, ertapenem, imipenem, meropenem, and panipenem.
 7. The method of claim 2, wherein the compound is 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 8. The method of claim 2, wherein the compound is 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 9. The method of claim 2, wherein the compound is 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 10. The method of claim 2, wherein the compound is 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 11. The method of claim 2, wherein the compound is 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 12. The method of claim 2, wherein the compound is 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 13. The method of claim 2, wherein the compound is 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 14. The method of claim 2, wherein the compound is 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 15. The method of claim 2, wherein the compound is 7-({1-[amino(l H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 16. The method of claim 2, wherein the compound is 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 17. A compound selected from the group of compounds consisting of: a) 7-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

b) 8-[(1-{[4-(2-aminoethyl)-1H-imidazol-1-yl]acetyl}azetidin-3-yl)oxy]-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

c) 7-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

d) 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

e) 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

f) 8-({1-[(2S)-2-amino-2-(H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

g) 7-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

h) 8-({1-[amino(1-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

i) 7-({1-[2-amino-2-(1H-imidazol-4-yl)(2H)ethanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

j) 8-({1-[2-amino-2-(1H-imidazol-4-yl)(2H)ethanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

k) 7-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

l) 8-({1-[2-amino-2-(1H-imidazol-4-yl)propanoyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

m) 7-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

n) 8-({1-[amino(2-methyl-1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

o) 2-hydroxy-7-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

p) 4,4-dihydroxy-8-({1-[(1H-1,2,3-triazol-1-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

q) 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

r) 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

s) 2-hydroxy-7-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

t) 4,4-dihydroxy-8-{[1-(4-hydroxyprolyl)azetidin-3-yl]oxy}-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

u) 2-hydroxy-7-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

v) 4,4-dihydroxy-8-({1-[(pyrrolidin-3-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

w) 2-hydroxy-7-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

x) 4,4-dihydroxy-8-({1-[(morpholin-2-yl)acetyl]azetidin-3-yl}oxy)-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

y) 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

z) 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

aa) 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid

ab) 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid

or a pharmaceutically acceptable salt thereof.
 18. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 7-({-[1-(2R)-2-amino-2-(H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid.
 19. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 8-({1-[(2R)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid.
 20. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 7-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid.
 21. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 8-({1-[(2S)-2-amino-2-(1H-imidazol-4-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid.
 22. The compound or the pharmaceutically acceptable salt thereof of claim 5, wherein the compound is 2-hydroxy-7-[(1-D-serylazetidin-3-yl)oxy]-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid.
 23. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 4,4-dihydroxy-8-[(1-D-serylazetidin-3-yl)oxy]-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid.
 24. The compound or the pharmaceutically acceptable salt thereof of claim 5, wherein the compound is 7-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid.
 25. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 8-{[1-(L-α-asparaginyl)azetidin-3-yl]oxy}-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid.
 26. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 7-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-2-hydroxy-3,4-dihydro-2H-1,2-benzoxaborinine-8-carboxylic acid.
 27. The compound or the pharmaceutically acceptable salt thereof of claim 17, wherein the compound is 8-({1-[amino(1H-imidazol-5-yl)acetyl]azetidin-3-yl}oxy)-4,4-dihydroxy-5-oxa-4-boranuidabicyclo[4.4.0]deca-l(6),7,9-triene-7-carboxylic acid. 